Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

ABSTRACT

Provided are a compound of Formula 1 and an organic electric element including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode and comprising the compound, the element showing improved luminescence efficiency, stability, and life span.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims benefit under 35 U.S.C. 119(e), 120, 121,or 365(c), and is a National Stage entry from International ApplicationNo. PCT/KR2015/001801 filed on Feb. 25, 2015, which claims priority toKorean Patent Application No. 10-2014-0023356 filed on Feb. 27, 2014,Korean Patent Application No. 10-2014-0064727 filed on May 28, 2014, andKorean Patent Application No. 10-2015-0025588 filed on Feb. 24, 2015,the contents of which are hereby incorporated by reference for allpurposes as if fully set forth herein.

BACKGROUND Technical Field

The present invention relates to compounds for organic electricelements, organic electric elements using the same, and electronicdevices thereof.

Background Art

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy of an organicmaterial. An organic electric element utilizing the organic lightemitting phenomenon usually has a structure including an anode, acathode, and an organic material layer interposed therebetween. In manycases, the organic material layer may have a multilayered structureincluding multiple layers made of different materials in order toimprove the efficiency and stability of an organic electric element, andfor example, may include a hole injection layer, a hole transport layer,a light emitting layer, an electron transport layer, an electroninjection layer, or the like.

A material used as an organic material layer in an organic electricelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function.

Currently, the power consumption is required more and more as size ofdisplay becomes larger and larger in the portable display market.Therefore, the power consumption is a very important factor in theportable display with a limited power source of the battery, andefficiency and life span issue also must be solved.

Efficiency, life span, driving voltage, and the like are correlated witheach other. For example, if efficiency is increased, then drivingvoltage is relatively lowered, and the crystallization of an organicmaterial due to Joule heating generated during operation is reduced asdriving voltage is lowered, as a result of which life span shows atendency to increase.

However, efficiency cannot be maximized only by simply improving theorganic material layer. This is because long life span and highefficiency can be simultaneously achieved when an optimal combination ofenergy levels and T1 values, inherent material properties (mobility,interfacial properties, etc.), and the like among the respective layersincluded in the organic material layer is given. Therefore it isrequired to develop a light emitting material that has high thermalstability and can achieve efficiently a charge balance in thelight-emitting layer.

Further, in order to solve the emission problem with a hole transportlayer in a recent organic electric element, an emission-auxiliary layeris present between the hole transport layer and a light emitting layer,and it is time to develop different emission-auxiliary layers accordingto respective light emitting layers (R, G, B).

In general, an electron transferred from an electron transport layer toa light emitting layer and a hole transferred from a hole transportlayer to the light emitting layer are recombined to form an exciton.

However, since a material used in a hole transporting layer should havea low HOMO value, it mainly has a low T1 value. Due to this, excitonsgenerated from a light emitting layer are transported to the holetransporting layer, resulting in a charge unbalance in the lightemitting layer. Thus, light emission occurs in the hole transportinglayer or at an interface of the hole transporting layer so that theorganic electroluminescent device is reduced in color purity,efficiency, and lifespan.

Also, when using a material having rapid hole mobility for reducing adriving voltage, this is tend to decrease the efficiency. In an OLEDs, acharge unbalance in the light emitting layer is caused because of thathole mobility is faster than electron mobility, and reduced efficiencyand lifespan is happened.

Therefore, an emitting auxiliary layer must be formed by a material whatcan solve the problems of an hole transport layer, having hole mobility(within the driving voltage range of the blue element of full device) togive the suitable driving voltage, high T1 energy value(electron block)and wide band gap. These requirements are not satisfied only bystructural characteristics about a core of the emitting auxiliarylayer's material. Therefore, it is necessary to develop of the materialfor the emitting auxiliary layer having high T1 energy value and wideband gap, to improve efficiency and lifespan of the organic electricelement as combined core of material and characteristics of subsubstituents appropriately.

In order to allow an organic electric element to fully exhibit theabove-mentioned excellent features, it should be prerequisite to supporta material constituting an organic material layer in the element, forexample, a hole injection material, a hole transport material, a lightemitting material, an electron transport material, an electron injectionmaterial, or the like, by a stable and efficient material. However, sucha stable and efficient organic material layer material for an organicelectric element has not yet been fully developed. Accordingly, there isa continuous need to develop new materials for an organic materiallayer.

SUMMARY

In order to solve one or more of the above-mentioned problems occurringin the prior art, an aspect of the present invention is to provide acompound which allows an organic electric element to improve inluminescence efficiency, stability and lifespan, an organic electricelement containing the same, and an electronic device including theorganic electric element.

In accordance with an aspect of the present invention, the compoundrepresented by the following Formula is provided.

In another aspect of the present invention, organic electric elementscontaining the compound represented by the formula above and electronicdevices including the organic electric element are provided.

By employing the compound of the present invention that has wide bandgap and high T1 energy value due to the non-linear linker(L) attached tothe carbazole core, the organic electric element according to one ormore embodiments of the present invention can have not only highluminescence efficiency and high heat-resistance, but also significantlyimproved color purity and lifespan.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates an example of an organic light emitting diodeaccording to an embodiment of the present invention.

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings.

In designation of reference numerals to components in respectivedrawings, it should be noted that the same elements will be designatedby the same reference numerals although they are shown in differentdrawings. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component. In addition, itwill be understood that when an element such as a layer, film, region orsubstrate is referred to as being “on” or “over” another element, it canbe directly on the other element or intervening elements may also bepresent. In contrast, when an element is referred to as being “directlyon” another element, there are no intervening elements present.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen” as used hereinincludes fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

Unless otherwise stated, the term “alkyl” or “alkyl group” as usedherein has a single bond of 1 to 60 carbon atoms, and means aliphaticfunctional radicals including a linear alkyl group, a branched chainalkyl group, a cyclo alkyl group (alicyclic), or an alkyl groupsubstituted with a cyclo alkyl.

Unless otherwise stated, the term “halo alkyl” or “halogen alkyl” asused herein includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “alkenyl” or “alkynyl” as used hereinhas, but not limited to, double or triple bonds of 2 to 60 carbon atoms,and includes a linear alkyl group, or a branched chain alkyl group.

Unless otherwise stated, the term “cyclo alkyl” as used herein means,but not limited to, alkyl forming a ring having 3 to 60 carbon atoms.

The term “alkoxyl group”, “alkoxy group” or “alkyloxy group” as usedherein means an oxygen radical attached to an alkyl group, but notlimited to, and has 1 to 60 carbon atoms.

The term “alkenoxyl group”, “alkenoxy group”, “alkenyloxyl group” or“alkenyloxy group” as used herein means an oxygen radical attached to analkyl group, but not limited to, and has 2 to 60 carbon atoms.

The term “aryloxyl group” or “aryloxy group” as used herein means anoxygen radical attached to an aryl group, but not limited to, and has 6to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to 60 carbon atoms. Herein, thearyl group or arylene group means a monocyclic or polycyclic aromaticgroup, and may also be formed in conjunction with an adjacent group.Examples of “aryl group” or “arylene group” may include a phenyl group,a biphenyl group, a fluorene group, or a spirofluorene group or aspirobifluorene group.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an aryl alkoxymeans an alkoxy substituted with an aryl, an alkoxyl carbonyl means acarbonyl substituted with an alkoxyl, and an aryl carbonyl alkenyl alsomeans an alkenyl substitutes with an aryl carbonyl, wherein the arylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the “hetero aryl group” or “hetero arylenegroup” as used herein means, but not limited to, a ring containing oneor more hetero atoms, and having 2 to 60 carbon atoms. They include atleast one monocyclic or polycyclic ring, and may be linked together toform a fused ring.

Unless otherwise stated, the term “heterocyclic group” as used hereinmeans, but not limited to, a ring containing one or more hetero atoms,and having 2 to 60 carbon atoms. They include at least one monocyclic orpolycyclic ring, and hetero aliphatic or hetero aromatic ring, and maybe linked together to form a fused ring.

Unless otherwise stated, the term “heteroatom” as used herein representsat least one of N, O, S, P, and Si.

Also, the term “heterocyclic group” may include SO₂ instead of carbonconsisting of cycle. For example, “heterocyclic group” includes compoundbelow.

Unless otherwise stated, the term “aliphatic” as used herein meansaliphatic hydrocarbon, having 1 to 60 carbon atoms. The term “aliphaticring” means aliphatic hydrocarbon ring, having 1 to 60 carbon.

Unless otherwise stated, the term “ring” as used herein means aliphaticring having 3 to 60 carbon or aromatic ring having 6 to 60 carbon, orheterocyclic ring having 2 to 60 carbon or a fused ring formed bycombinations thereof, includes saturated or unsaturated ring.

The other hetero cyclic compounds or hetero radicals may include, butnot limited to, at least one hetero atom, except to the described heterocyclic compound above.

Unless otherwise stated, the term “substituted or unsubstituted” as usedherein means that substitution is carried out by at least onesubstituent selected from the group consisting of, but not limited to,deuterium, halogen, an amino group, a nitrile group, a nitro group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylamine group, aC₁-C₂₀ alkylthio group, a C₆-C₂₀ arylthio group, a C₂-C₂₀ alkenyl group,a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, a C₆-C₆₀ aryl group,a C₆-C₂₀ aryl group substituted by deuterium, a C₈-C₂₀ arylalkenylgroup, a silane group, a boron group, a germanium group, and a C₂-C₂₀heterocyclic group.

Otherwise specified, the Formulas used in the present invention are asdefined in the index definition of the substituent of the followingFormula.

Wherein, when a is an integer of zero, the substituent R¹ is absent,when a is an integer of 1, the sole R¹ is linked to any one of thecarbon atoms constituting the benzene ring, when a is an integer of 2 or3, the substituent R¹s may be the same and different, and are linked tothe benzene ring as follows. when a is an integer of 4 to 6, thesubstituents R¹s may be the same and different, and are linked to thebenzene ring in a similar manner to that when a is an integer of 2 or 3,hydrogen atoms linked to carbon constituents of the benzene ring beingnot represented as usual.

FIG. 1 illustrates an organic electric element according to anembodiment of the present invention.

Referring to FIG. 1, an organic electric element 100 according to anembodiment of the present invention includes a first electrode 120formed on a substrate 110, a second electrode 180, and an organicmaterial layer between the first electrode 110 and the second electrode180, which contains the inventive compound. Here, the first electrode120 may be an anode (positive electrode), and the second electrode 180may be a cathode (negative electrode). In the case of an invertedorganic electric element, the first electrode may be a cathode, and thesecond electrode may be an anode.

The organic material layer includes a hole injection layer 130, a holetransport layer 140, a light emitting layer 150, an electron transportlayer 160, and an electron injection layer 170 formed in sequence on thefirst electrode 120. Here, the layers included in the organic materiallayer, except the light emitting layer 150, may not be formed. Theorganic material layer may further include a hole blocking layer, anelectron blocking layer, an emission-auxiliary layer 151, a buffer layer141, etc., and the electron transport layer 160 and the like may serveas the hole blocking layer.

Although not shown, the organic electric element according to anembodiment of the present invention may further include at least oneprotective layer or one capping layer formed on at least one of thesides the first and second electrodes, which is a side opposite to theorganic material layer.

The inventive compound employed in the organic material layer may beused as a host material, a dopant material, or a capping layer materialin the hole injection layer 130, the hole transport layer 140, theelectron transport layer 160, the electron injection layer 170, or thelight emitting layer 150. For example, the inventive compound may beused as the light emitting layer 150, the hole transport layer 140,and/or the emission-auxiliary layer 151.

Since depending on the type and position of a substituent to beattached, a band gap, electrical properties, interfacial properties, andthe like may vary even in the same core, it is very important what thetypes of core and a combination of substituent attached to the core are.Specially, long life span and high efficiency can be simultaneouslyachieved when an optimal combination of energy levels and T1 values,inherent material properties (mobility, interfacial properties, etc.),and the like among the respective layers included in the organicmaterial layer is given.

As already described above, in order to solve the emission problem witha hole transport layer in a conventional organic electric element, anemission-auxiliary layer is preferably formed between the hole transportlayer and a light emitting layer, and it is time to develop differentemission-auxiliary layers according to respective light emitting layers(R, G, B). However, even when a similar core is used, it is verydifficult to infer the characteristics of an emission-auxiliary layer ifa used organic material layer varies because the correlation between theemission-auxiliary layer and a hole transport layer and the correlationbetween the emission-auxiliary layer and a light emitting layer (host)mused be discovered.

Accordingly, in the present invention, a combination of energy levelsand T1 values, inherent material properties (mobility, interfacialproperties, etc.), and the like among the respective layers included inthe organic material layer is optimized by forming a light emittinglayer and/or an emission-auxiliary layer by using the compoundrepresented by Formula 1, and thus the life span and efficiency of theorganic electric element can be improved at the same time.

The organic electric element according to an embodiment of the presentinvention may be manufactured using various deposition methods. Theorganic electric element according to an embodiment of the presentinvention may be manufactured using a PVD(physical vapor deposition)method or CVD(chemical vapor deposition) method. For example, theorganic electric element may be manufactured by depositing a metal, aconductive metal oxide, or a mixture thereof on the substrate to formthe anode 120, forming the organic material layer including the holeinjection layer 130, the hole transport layer 140, the light emittinglayer 150, the electron transport layer 160, and the electron injectionlayer 170 thereon, and then depositing a material, which can be used asthe cathode 180, thereon. Also, an emitting auxiliary layer 151 may becomprised between the hole transport layer 140 and the light emittinglayer 150.

And also, the organic material layer may be manufactured in such amanner that a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, dip coating, doctor blading, screen printing, inkjet printing,or thermal transfer, instead of deposition. Since the organic materiallayer according to the present invention may be formed in various ways,the scope of protection of the present invention is not limited by amethod of forming the organic material layer.

According to used materials, the organic electric element according toan embodiment of the present invention may be of a top emission type, abottom emission type, or a dual emission type.

A WOLED (White Organic Light Emitting Device) readily allows for theformation of ultra-high definition images, and is of excellentprocessability as well as enjoying the advantage of being produced usingconventional color filter technologies for LCDs. In this regard, variousstructures for WOLEDs, used as back light units, have been, in the mostpart, suggested and patented. Representative among the structures are aparallel side-by-side arrangement of R(Red), G(Green), B(Blue)light-emitting units, a vertical stack arrangement of RGB light-emittingunits, and a CCM (color conversion material) structure in whichelectroluminescence from a blue (B) organic light emitting layer, andphotoluminescence from an inorganic luminescent using theelectroluminescence are combined. The present invention is applicable tothese WOLEDs.

Further, the organic electric element according to an embodiment of thepresent invention may be any one of an organic light emitting diode(OLED), an organic solar cell, an organic photo conductor (OPC), anorganic transistor (organic TFT), and an element for monochromatic orwhite illumination.

Another embodiment of the present invention provides an electronicdevice including a display device, which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, an organic electric element according to an aspect of thepresent invention will be described.

The compound according to an aspect of the present invention isrepresented by the following Formula 1.

In Formula 1 above, Ar¹ to Ar³ may be each independently selected fromthe group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P; a fused ring formed by a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; anda C₆-C₃₀ aryloxy group. For example, Ar¹ to Ar³ may be eachindependently phenyl, naphthyl, biphenyl, terphenyl, phenyl substitutedwith deuterium, methyl phenyl, t-butyl phenyl, methoxy phenyl, terphenylsubstituted with deuterium, 9,9-dimethyl-9H-fluorenyl,9,9-diphenyl-9H-fluorenyl, 7,7-diphenyl-7H-benzo[c]fluorenyl,spirobifluorenyl, 9-phenyl-9H-carbazolyl, 9-naphthyl-9H-carbazolyl,9-biphenyl-9H-carbazolyl, 9-triazinyl-9H-carbazolyl,9-dibenzothienyl-9H-carbazolyl, 7-phenyl-7H-benzo[c]carbazolyl,5-phenyl-5H-benzo[b]carbazolyl, 11-phenyl-11H-benzo[a]carbazolyl,dibenzothienyl, dibenzofuryl, naphto[2,1-b]benzothienyl,naphto[2,1-b]benzofuryl or phenylpyrimidinyl.

L may be

wherein, R³ may be selected from the group consisting of i)deuterium;halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si, and P; a fused ring formed by a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; aC₆-C₃₀ aryloxy group; -L′-N(R^(a)) (R^(b)); and combinations thereof, orii) two adjacent groups, may be optionally linked together to form atleast one ring, and the group(s) of R³s not forming a ring may be thesame as defined in the above i). For example, R³ may be phenyl,biphenyl, naphthyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl,quinazolyl, or adjacent R³s may be linked together to form at least onearomatic ring such as naphthalene or phenanthrene, or hetero cyclic ringsuch as isoquinoline, quinoline, quinazoline or quinoxaline with thebenzene ring to which R³s are attached.

o may be an integer of 0 to 4, plural R³s may be same or different eachother when o is 2 or more. And all of or some of the adjacent groups,R³s, may be linked together to form a ring, and the group(s) of R³s notforming a ring may be any one of substituents as defined in the abovei).

In Formula 1 above, m may be an integer of 0 to 4, and n may be aninteger of 0 to 3.

R¹ and R² may be each independently selected from the group consistingof i) deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; aC₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P; a fused ring formed bya C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkylgroup; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxygroup; a C₆-C₃₀ aryloxy group; and -L′-N(R^(a)) (R^(b)), or ii) any twoadjacent groups may be optionally linked together to form at least onering, and the group(s) of R¹ and R² not forming a ring may be the sameas defined in the above i). For example, R¹ and R² may be eachindependently propenyl, phenyl, dibenzothienyl, triazinyl, quinolyl orquinazolyl, adjacent R¹s and/or R²s may be linked together to form anaromatic ring such as naphthalene or phenanthrene, or hetero cyclic ringsuch as isoquinoline, quinoline, quinazoline or quinoxaline, with thebenzene ring to which they are attached.

Plural R¹s may be same or different each other when m is 2 or more, andall of some of the adjacent groups, R¹s, may be linked together to forma ring. The same applies to plural R²s where n is 2 or more, and all ofor some of the adjacent groups, R²s, may be linked together to form aring.

Meanwhile, a fused ring formed by adjacent groups may be a C₃-C₆₀aliphatic ring or a C₆-C₆₀ aromatic ring, a C₂-C₆₀ hetero cyclic ring, aC₃-C₆₀ alicyclic ring, or a fused ring formed y combinations thereof,and it may be a monocyclic or polycyclic ring, and/or a saturated orunsaturated ring.

L′ may be selected from the group consisting of single bond; a C₆-C₆₀arylene group; a fluorenylene group; a fused ring formed by a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si, and P, R^(a) and R^(b) may be eachindependently selected from the group consisting of C₆-C₆₀ aryl group; afluorenyl group; a fused ring formed by a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P.

For example, in Formula 1 above, Ar¹ may be selected from the followingstructures:

wherein R′ and R″ may be each independently selected from the groupconsisting of hydrogen; deuterium; tritium; a C₆-C₂₀ aryl group; aC₁-C₂₀ alkyl group; and a C₂-C₂₀ alkenyl group. For example, R′ and R″may be each independently methyl or phenyl, and R′ and R″ may be linkedtogether to form a spiro compound with the carbon to which they areattached.

R⁴ and R⁵ may be each independently selected from the group consistingof deuterium; tritium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group;a C₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P; a fused ring formed bya C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkylgroup; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxylgroup; and a C₆-C₃₀ aryloxy group, and any two adjacent groups may beoptionally linked together to form at least one ring. Herein, the groupsof R⁴s and R⁵s not forming a ring may be the same as defined in theabove.

p may be an integer of 0 to 4, q may be an integer of 0 to 3. When pand/or q are 2 or more, plural R⁴s may be same or different each other,and plural R⁵s may be same or different each other. Further, all of orsome of adjacent R⁴s may be linked together to form one or more ring,and all of or some of adjacent R⁵s may be linked together to form one ormore ring. Furthermore, for example, adjacent R⁴s may be linked togetherto form a ring, and adjacent R⁵s may be each independently aryl group orhetero cyclic ring.

The ring formed by linking between adjacent groups may be a C₃-C₆₀aliphatic ring or a C₆-C₆₀ aromatic ring, a C₂-C₆₀ hetero ring, a C₃-C₆₀alicyclic ring, or a fused ring formed by combinations thereof, and thering may be a mono cyclic or poly cyclic ring, and/or saturated orunsaturated ring.

Also, Ar² and Ar³ in Formula 1 above may be selected from the followingstructures:

wherein, Ar⁴ may be selected from the group consisting of a C₆-C₆₀ arylgroup; a fluorenyl group; and a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P. For example, Ar⁴ may be phenyl, biphenyl, naphthyl, pyridyl,9,9-dimethyl-9H-fluorenyl, triazinyl, phenyl substituted with deuterium,or dibenzothienyl.

R⁶ and R⁷ may be each independently selected from the group consistingof deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P; a fused ring formed by a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; aC₆-C₃₀ aryloxy group; and -L′-N(R^(a)) (R^(b)). Herein L′, R^(a) andR^(b) may be the same as defined in above R¹ to R³.

Further, any two adjacent R⁶s and R⁷s may be independently linkedtogether to form at least one ring, and the groups of R⁶s and R⁷s notforming a ring may be the same as defined in the above. For example,adjacent R⁶s and/or R⁷s may be optionally linked together to form anaromatic ring such as naphthalene or phenanthrene, or hetero cyclic ringsuch as isoquinoline, quinoline, quinazoline or quinoxaline, with thebenzene ring to which they are attached.

Further, a may be an integer of 0 to 4, b may be an integer of 0 to 3.wherein each of plural R⁶s and plural R⁷s may be same or different eachother when a and b are each 2 or more. All of or some of adjacent R⁶smay be linked together to form at least one ring, all of or some ofadjacent R⁷s may be linked together to form at least one ring, and eventhough adjacent R⁶s may be linked together to form a ring, adjacent R⁷smay be each independently aryl group or hetero cyclic ring.

The ring formed by adjacent groups may be a C₃-C₆₀ aliphatic ring or aC₆-C₆₀ aromatic ring, a C₂-C₆₀ hetero ring, a C₃-C₆₀ alicyclic ring, ora fused ring formed by combinations thereof, and it may be a mono cyclicor poly cyclic ring, and/or saturated or unsaturated ring.

Each of the above aryl group, fluorenyl group, heterocyclic group, fusedring group, alkyl group, alkenyl group, alkynyl group, alkoxy group,aryloxy group, arylene group and fluorenylene group may be substitutedwith one or more substituents selected from the group consisting ofdeuterium; halogen; a silane group; a siloxane group; a boron group; agermanium group; a cyano group; a nitro group; a C₁-C₂₀ alkylthio group;a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; aC₂-C₂₀ alkynyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀ aryl groupsubstituted with deuterium; a fluorenyl group; a C₂-C₂₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si, and P; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀arylalkyl group; and a C₈-C₂₀ arylalkenyl group.

Specifically, the compounds represented by Formula 1 above may berepresented any one of the following Formulas, and the followingFormulas represent the cases when adjacent R¹s and/or adjacent R²s maybe linked together to form a ring.

In Formulas 2 to 10 above, each symbols of Ar¹ to Ar³, L, R¹, m and nmay be the same as defined in Formula 1 above.

Specifically, the compounds represented by Formula 1 above may berepresented any one of the following Formulas:

In Formulas 11 to 20, each symbols of Ar², Ar³, L, R¹, R², m, and n maybe the same as defined in Formula 1 above.

R⁴ and R⁵ may be each independently selected from the group consistingof hydrogen; deuterium; tritium; halogen; a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P; afused ring formed by a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring;a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₁-C₃₀ alkoxy group; and a C₆-C₃₀ aryloxy group, or the adjacent groupsmay be optionally linked together to form at least one ring. Herein, thegroup(s) not forming a ring may be the same as defined in the above.

X may be O, S or C(R′) (R″), and R′ and R″ may be the same as defined inthe structural formula of Ar¹ above. This is, R′ and R″ may be eachindependently selected from the group consisting of hydrogen; deuterium;tritium; a C₆-C₂₀ aryl group; a C₁-C₂₀ alkyl group; and a C₂-C₂₀ alkenylgroup. Further, R′ and R″ may be optionally linked together to form aspiro compound with the carbon to which they are attached.

The Formula 1 may be represented by the following formula:

In Formula 21 above, the symbols are defined as the same in Formula 1above. For example, R¹, R², m, n, Ar¹, Ar³, L and the like may be thesame as defined in Formula 1 above. Ar⁴ may be the same as defined inthe structural formula of Ar² above. This is, Ar⁴ may be selected fromthe group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; and aC₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P.

R⁶, R⁷, a, and b may be the same as defined in the structure of Ar²above. This is, R⁶ and R⁷ may be each independently selected from thegroup consisting of i) deuterium; halogen; a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P; afused ring formed by a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring;a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₁-C₃₀ alkoxy group; a C₆-C₃₀ aryloxy group; and -L′-N(R^(a)) (R^(b)),herein, L′ may be selected from the group consisting of single bond; aC₆-C₆₀ arylene group; a fluorenylene group; a fused ring formed by aC₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, and R^(a) and R^(b) may be eachindependently selected from the group consisting of a C₆-C₆₀ aryl group;a fluorenyl group; a fused ring formed by a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P. ii) adjacent groups of R⁶ and R⁷ may be optionally linkedtogether to form at least one ring, and the group of R⁶s and R⁷s notforming a ring may be the same as defined in above i).

Further, a may be an integer of 0 to 4, and R⁶ may be same or differenteach other when a is 2 or more, b may be an integer of 0 to 3, and R⁷may be same or different each other when b is 2 or more.

More specifically, the above Formula 21 may represent any one of thefollowing formulas:

In Formulas 22 and 23, the symbols are defined as the same in Formula 1or 21 above.

More specifically, the compounds represented by Formulas 1 to 21 may beany one of the following compounds.

In another aspect of the present invention, a compound for an organicelectric element represented by Formula 1 above is provided.

In another aspect of the present invention, an organic electric elementcomprising the compound represented by Formula 1 above is provided.

The organic electric element can comprise a first electrode, a secondelectrode, and an organic material layer disposed between the firstelectrode and the second electrode. The organic material layer cancomprise the compound represented by Formula 1. The compound representedFormula 1 can be contained in at least one layer of a hole injectionlayer, a hole transport layer, an emission-auxiliary layer and a lightemitting layer of the organic material layer. That is, the compoundrepresented by Formula 1 may be used as a material in the hole injectionlayer, a material in the hole transport layer, a material in theemission-auxiliary layer, or a material in the light emitting layer,preferably, as a material a hole transport layer and/or anemission-auxiliary layer.

Specifically, the organic electric element comprising the organicmaterial layer comprising at least one of the compounds represented byFormula 2 to 23 is provided, and more specifically, the organic electricelement comprising the organic material layer comprising at least one ofthe compounds P1-1 to P1-112, P2-1 to P2-112, P3-1 to P3-39 and P4-1 toP4-36 is provided.

Furthermore, the compounds comprising of an organic material layer canbe one kind or two or more different kinds of the compounds representedby Formula 1 above. For example, a hole transport layer and/or anemission-auxiliary layer of an organic material layer may be formed as asingle kind, 2 or more different kinds of individual compounds P1-1 orP1-2, or 3 or more different kinds of compound P1-1, P1-2 and P1-3.

In another aspect of the present invention, the present inventionprovides an organic electric element further including at least a layerto improve luminescence efficiency which is formed on at least one ofthe sides the first and second electrodes, which is opposite to theorganic material layer.

Hereinafter, Synthesis Examples of the inventive compound represented byFormula 1 above and Preparation Examples of an organic electric elementwill be described in detail by way of example. However, the followingexamples are only for illustrative purposes and are not intended tolimit the scope of the invention.

SYNTHESIS EXAMPLE

The final product of the present invention can be synthesized byreaction of Sub 1 and Sub 2 as illustrated in the following ReactionScheme 1, but the present invention is not limited to the followingexamples.

I. Synthesis Example of Sub 1

Sub 1 of the Reaction Scheme 1 can be synthesized according to, but notlimited to, the following Reaction Scheme 2.

1. Synthesis Example of Sub 1-1

(1) Synthesis of Sub 1-I-1

Phenylboronic acid (76.84 g, 630.2 mmol) was dissolved in THF (2780 ml)in a round bottom flask. Then, 4-bromo-1-iodo-2-nitrobenzene (309.96 g,945.3 mmol), Pd(PPh₃)₄ (36.41 g, 31.5 mmol), K₂CO₃ (261.3 g, 1890.6mmol) and water (1390 ml) were added into the round bottom flask, andthe mixture was stirred at 80° C. After the completion of the reaction,the reaction product was extracted with CH₂Cl₂ and water. The extractedorganic layer was dried over MgSO₄ and concentrated. The concentratedresultant was separated by silica gel column chromatography, and wasthen recrystallized, whereby a compound Sub 1-I-1 was obtained in anamount of 122.68 g in 70% yield.

(2) Synthesis of Sub 1-II-1

The compound Sub 1-I-1 (122.68 g, 441.1 mmol) obtained above wasdissolved in o-dichlorobenzene (1810 ml) in a round bottom flask. Then,triphenylphosphine (289.26 g, 1102.8 mmol) was added into the roundbottom flask, and the mixture was stirred at 200° C. After thecompletion of the reaction, o-dichlorobenzene from the reaction productwas removed by distillation and the reaction product was extracted withCH₂Cl₂ and water. The extracted organic layer was dried over MgSO₄ andconcentrated. The concentrated resultant was separated by silica gelcolumn chromatography, and was then recrystallized, whereby a compoundSub 1-II-1 was obtained in an amount of 80.34 g in 74% yield.

(3) Synthesis of Sub 1-III-1

The compound Sub 1-II-1 (80.34 g, 326.5 mmol) obtained above wasdissolved in nitrobenzene (653 ml) in a round bottom flask. Then,iodobenzene (99.9 g, 489.7 mmol), Na₂SO₄ (46.37 g, 326.5 mmol), K₂CO₃(45.12 g, 326.5 mmol) and Cu (6.22 g, 97.9 mmol) were added into theround bottom flask, and the mixture was stirred at 200° C. After thecompletion of the reaction, nitrobenzene from the reaction product wasremoved by distillation and the reaction product was extracted withCH₂Cl₂ and water. The extracted organic layer was dried over MgSO₄ andconcentrated. The concentrated resultant was separated by silica gelcolumn chromatography, and was then recrystallized, whereby a compoundSub 1-III-1 was obtained in an amount of 76.78 g in 73% yield.

(4) Synthesis of Sub 1-IV-1

The compound Sub 11-III-1 (76.78 g, 238.3 mmol) obtained above wasdissolved in DMF in a round bottom flask. Then, Bis(pinacolato)diboron(66.57 g, 262.1 mmol), Pd(dppf)C12 (5.84 g,7.1 mmol) and KOAc (70.16 g,714.9 mmol) were added into the round bottom flask, and the mixture wasstirred at 90° C. After the completion of the reaction, DMF from thereaction product was removed by distillation and the reaction productwas extracted with CH₂Cl₂ and water. The extracted organic layer wasdried over MgSO₄ and concentrated. The concentrated resultant wasseparated by silica gel column chromatography, and was thenrecrystallized, whereby a compound Sub 1-IV-1 was obtained in an amountof 73.92 g in 84% yield.

(5) Synthesis of Sub 1-1

The compound Sub 1-IV-1 (73.92 g, 200.2 mmol) obtained above wasdissolved in THF (880 ml) in a round bottom flask. Then,1-bromo-2-iodobenzene (85.0 g, 300.3 mmol), Pd(PPh₃)₄ (11.6 g, 10 mmol),K₂CO₃ (83 g, 600.6 mmol) and water (440 mL) were added into the roundbottom flask, and the mixture was stirred at 80° C. After the completionof the reaction, the reaction product was extracted with CH₂Cl₂ andwater. The extracted organic layer was dried over MgSO₄ andconcentrated. The concentrated resultant was separated by silica gelcolumn chromatography, and was then recrystallized, whereby a compoundSub 1-1 was obtained in an amount of 55.8 g in 70% yield.

2. Synthesis Examples of Sub 1-7

(1) Synthesis of Sub 1-I-7

The compound Sub 1-I-7 was synthesized by using(4-(dibenzo[b,d]thiophen-2-yl)phenyl)boronic acid (95.8 g, 315.1 mmol),THF (1390 ml), 4-bromo-1-iodo-2-nitrobenzene (155 g, 472.7 mmol),Pd(PPh₃)₄ (18.2 g, 15.8 mmol), K₂CO₃ (130.7 g, 945.3 mmol) and water(695 ml) in the same manner as described in the synthesis method of thecompound Sub 1-I-1 above, whereby a compound Sub 1-I-7 was obtained inan amount of 103 g in 71% yield.

(2) Synthesis of Sub 1-II-7

The compound Sub 1-II-7 was synthesized by using Sub 1-I-7 (103 g, 223.7mmol), o-dichlorobenzene (917 ml), and triphenylphosphine (146.7 g,559.3 mmol) in the same manner as described in the synthesis method ofthe compound Sub 1-II-1 above, whereby a compound Sub 1-II-7 wasobtained in an amount of 69 g in 72% yield.

(3) Synthesis of Sub 1-III-7

The compound Sub 1-III-7 was synthesized by using Sub 1-II-7 (69 g,161.1 mmol), nitrobenzene (322 ml), iodobenzene (49.4 g, 242 mmol),Na₂SO₄ (22.9 g, 161.1 mmol), K₂CO₃ (22.3 g, 161.1 mmol) and Cu (3.1 g,48.3 mmol) in the same manner as described in the synthesis method ofthe compound Sub 1-III-1 above, whereby a compound Sub 1-III-7 wasobtained in an amount of 57 g in 70% yield.

(4) Synthesis of Sub 1-IV-7

The compound Sub 1-IV-7 was synthesized by using Sub 1-III-7 (57 g, 113mmol), DMF (712 ml), Bis(pinacolato)diboron (31.6 g, 124.3 mmol),Pd(dppf)Cl₂ (2.8 g, 3.4 mmol) and KOAc (33.3 g, 339 mmol) in the samemanner as described in the synthesis method of the compound Sub 1-IV-1above, whereby a compound Sub 1-IV-7 was obtained in an amount of 49.2 gin 79% yield.

(5) Synthesis of Sub 1-7

The compound Sub 1-7 was synthesized by using Sub 1-IV-7 (49.2 g, 89.2mmol), 1-bromo-2-iodobenzene (39.9 g, 134 mmol), Pd(PPh₃)₄ (5.2 g, 4.5mmol), K₂CO₃ (37 g, 268 mmol), THF (392 ml) and water (196 ml) in thesame manner as described in the synthesis method of the compound Sub 1-1above, whereby a compound Sub 1-7 was obtained in an amount of 35.7 g in69% yield.

3. Synthesis Examples of Sub 1-13

(1) Synthesis of Sub 1-III-13

The compound Sub 1-III-13 was synthesized by using Sub 1-II-1 (70 g,284.4 mmol), nitrobenzene (570 ml), 2-iodo-9,9-diphenyl-9H-fluorene(189.6 g, 426.7 mmol), Na₂SO₄ (40.4 g, 284.4 mmol), K₂CO₃ (39.3 g, 284.4mmol) and Cu (5.42 g, 85.3 mmol) in the same manner as described in thesynthesis method of the compound Sub 1-III-1 above, whereby a compoundSub 1-III-13 was obtained in an amount of 108.8 g in 68% yield.

(2) Synthesis of Sub 1-IV-13

The compound Sub 1-IV-13 was synthesized by using (108.8 g, 193.4 mmol),DMF (1220 ml), Bis(pinacolato)diboron (54.0 g, 212.76 mmol), Pd(dppf)Cl₂(4.73 g, 5.8 mmol) and KOAc (56.94 g, 580.3 mmol) in the same manner asdescribed in the synthesis method of the compound Sub 1-IV-1 above,whereby a compound Sub 1-IV-13 was obtained in an amount of 86.1 g in73% yield.

(3) Synthesis of Sub 1-13

The compound Sub 1-13 was synthesized by using Sub 1-IV-13 (86.1 g,141.2 mmol), THF (620 ml), 1-bromo-2-iodobenzene (59.9 g, 211.9 mmol),Pd(PPh₃)₄ (8.2 g, 7.06 mmol), K₂CO₃ (58.6 g, 423.7 mmol) and water (310ml) in the same manner as described in the synthesis method of thecompound Sub 1-1 above, whereby a compound Sub 1-13 was obtained in anamount of 58.6 g in 65% yield.

4. Synthesis of Sub 1-14

(1) Synthesis of Sub 1-III-14

The compound Sub 1-III-14 was synthesized by using Sub 1-II-1 (63 g,255.9 mmol), nitrobenzene (512 ml), 3-iodo-9,9-diphenyl-9H-fluorene(170.6 g, 383.9 mmol), Na₂SO₄ (36.4 g, 256 mmol), K₂CO₃ (35.4 g, 256mmol) and Cu (4.88 g, 76.8 mmol) in the same manner as described in thesynthesis method of the compound Sub 1-III-1 above, whereby a compoundSub 1-III-14 was obtained in an amount of 99.3 g in 69% yield.

(2) Synthesis of Sub 1-IV-14

The compound Sub 1-IV-14 was synthesized by using Sub 1-III-14 (99.3 g,193.4 mmol), DMF (1110 ml), Bis(pinacolato)diboron (49.3 g, 194.2 mmol),Pd(dppf)Cl₂ (4.32 g, 5.3 mmol) and KOAc (52 g, 529.6 mmol) in the samemanner as described in the synthesis method of the compound Sub 1-IV-1above, whereby a compound Sub 1-IV-14 was obtained in an amount of 80.7g in 75% yield.

(3) Synthesis of Sub 1-14

The compound Sub 1-14 was synthesized by using Sub 1-IV-14 (80.7 g,132.3 mmol), THF (582 ml), 1-bromo-2-iodobenzene (56.2 g, 198.6 mmol),Pd(PPh₃)₄ (7.65 g, 6.62 mmol), K₂CO₃ (54.9 g, 397.2 mmol) and water (291ml) in the same manner as described in the synthesis method of thecompound Sub 1-1 above, whereby a compound Sub 1-14 was obtained in anamount of 52.4 g in 62% yield.

5. Synthesis of Sub 1-17

(1) Synthesis of Sub 1-III-17

The compound Sub 1-III-17 was synthesized by using Sub 1-II-1 (60 g, 244mmol), nitrobenzene (487 ml), 5′-iodo-1,1′:3′,1″-terphenyl (130.3 g,365.7 mmol), Na₂SO₄ (34.6 g, 244 mmol), K₂CO₃ (33.7 g, 244 mmol) and Cu(4.65 g, 73.1 mmol) in the same manner as described in the synthesismethod of the compound Sub 1-III-1 above, whereby a compound Sub1-III-17 was obtained in an amount of 82.1 g in 71% yield.

(2) Synthesis of Sub 1-IV-17

The compound Sub 1-IV-17 was synthesized by using Sub 1-III-17 (82.1 g,173.1 mmol), DMF (1090 ml), Bis(pinacolato)diboron (48.3 g, 190.4 mmol),Pd(dppf)Cl₂ (4.24 g, 5.2 mmol) and KOAc (51 g, 519.2 mmol) in the samemanner as described in the synthesis method of the compound Sub 1-IV-1above, whereby a compound Sub 1-IV-17 was obtained in an amount of 65.9g in 73% yield.

(3) Synthesis of Sub 1-17

The compound Sub 1-17 was synthesized by using Sub 1-IV-17 (65.9 g,126.4 mmol), THF (556 ml), 1-bromo-2-iodobenzene (53.8 g, 190 mmol),Pd(PPh₃)₄ (7.3 g, 6.32 mmol), K₂CO₃ (52.4 g, 319.1 mmol) and water (278ml) in the same manner as described in the synthesis method of thecompound Sub 1-1 above, whereby a compound Sub 1-17 was obtained in anamount of 45.2 g in 65% yield.

6. Synthesis of Sub 1-32

(1) Synthesis of Sub 1-I-32

The compound Sub 1-I-32 was synthesized by using naphthalen-1-ylboronicacid (70 g, 407 mmol), THF (1790 ml), 4-bromo-1-iodo-2-nitrobenzene (200g, 610.5 mmol), Pd(PPh₃)₄ (23.5 g, 20.35 mmol), K₂CO₃ (168.8 g, 1221mmol) and water (895 ml) in the same manner as described in thesynthesis method of the compound Sub 1-I-1 above, whereby a compound Sub1-I-32 was obtained in an amount of 94.8 g in 71% yield.

(2) Synthesis of Sub 1-II-32

The compound Sub 1-II-32 was synthesized by using Sub 1-I-32 (94.8 g,288.9 mmol), o-dichlorobenzene (1184 ml) and triphenylphosphine (189.4g, 722.2 mmol) in the same manner as described in the synthesis methodof the compound Sub 1-II-1 above, whereby a compound Sub 1-II-32 wasobtained in an amount of 61.2 g in 75% yield.

(3) Synthesis of Sub 1-III-32

The compound Sub 1-III-32 was synthesized by using Sub 1-II-32 (61.2 g,206.6 mmol), nitrobenzene (413 ml), 2-iodo-9,9-diphenyl-9H-fluorene(137.7 g, 310 mmol), Na₂SO₄ (29.35 g, 206.6 mmol), K₂CO₃ (28.6 g, 206.6mmol) and Cu (3.9 g, 62 mmol) in the same manner as described in thesynthesis method of the compound Sub 1-III-1 above, whereby a compoundSub 1-III-32 was obtained in an amount of 89.86 g in 71% yield.

(4) Synthesis of Sub 1-IV-32

The compound Sub 1-IV-32 was synthesized by using Sub 1-III-32 (89.86 g,146.7 mmol), DMF (924 ml), Bis(pinacolato)diboron (41 g, 161.4 mmol),Pd(dppf)Cl₂ (3.59 g, 4.4 mmol) and KOAc (43.2 g, 440.1 mmol) in the samemanner as described in the synthesis method of the compound Sub 1-IV-1above, whereby a compound Sub 1-IV-32 was obtained in an amount of 74.5g in 77% yield.

(5) Synthesis of Sub 1-32

The compound Sub Sub 1-32 was synthesized by using Sub 1-IV-32 (74.5 g,112.9 mmol), THF (496 ml), 2-iodobenzene (47.9 g, 169.4 mmol), Pd(PPh₃)₄(6.53 g, 5.65 mmol), K₂CO₃ (46.8 g, 338.8 mmol) and water (248 ml) inthe same manner as described in the synthesis method of the compound Sub1-1 above, whereby a compound Sub Sub 1-32 was obtained in an amount of47.4 g in 61% yield.

7. Synthesis of 1-34

(1) Synthesis of Sub 1-I-34

The compound Sub 1-I-34 was synthesized by using naphthalen-2-ylboronicacid (70 g, 407 mmol), THF (1790 ml), 4-bromo-1-iodo-2-nitrobenzene (200g, 610.5 mmol), Pd(PPh₃)₄ (23.5 g, 20.35 mmol), K₂CO₃ (168.8 g, 1221mmol) and water (895 ml) in the same manner as described in thesynthesis method of the compound Sub 1-I-1 above, whereby a compound Sub1-I-34 was obtained in an amount of 97.5 g in 73% yield.

(2) Synthesis of Sub 1-II-34

The compound Sub 1-II-34 was synthesized by using Sub 1-I-34 (97.5 g,297.1 mmol), o-dichlorobenzene (1220 ml) and triphenylphosphine (194.8g, 742.8 mmol) in the same manner as described in the synthesis methodof the compound Sub 1-II-1 above, whereby a compound Sub 1-II-34 wasobtained in an amount of 65.1 g in 74% yield.

(3) Synthesis of Sub 1-III-34

The compound Sub 1-III-34 was synthesized by using Sub 1-II-34 (65.1 g,220 mmol), nitrobenzene (440 ml), 3-iodo-9,9-diphenyl-9H-fluorene (146.5g, 330 mmol), Na₂SO₄ (31.2 g, 220 mmol), K₂CO₃ (30.4 g, 220 mmol) and Cu(4.2 g, 66 mmol) in the same manner as described in the synthesis methodof the compound Sub 1-III-1 above, whereby a compound Sub 1-III-34 wasobtained in an amount of 95.6 g in 71% yield.

(4) Synthesis of Sub 1-IV-34

The compound Sub 1-IV-34 was synthesized by using Sub 1-III-34 (95.6 g,156.1 mmol), DMF (980 ml), Bis(pinacolato)diboron (43.6 g, 171.7 mmol),Pd(dppf)Cl₂ (3.82 g, 4.7 mmol) and KOAc (46 g, 468.2 mmol) in the samemanner as described in the synthesis method of the compound Sub 1-IV-1above, whereby a compound Sub 1-IV-34 was obtained in an amount of 77.2g in 75% yield.

(5) Synthesis of Sub 1-34

The compound Sub 1-34 was synthesized by using Sub 1-IV-34 (77.2 g, 117mmol), THF (510 ml), 1-bromo-2-(49.7 g, 175.6 mmol), Pd(PPh₃)₄ (6.76 g,5.85 mmol), K₂CO₃ (48.5 g, 351 mmol) and water (255 ml) in the samemanner as described in the synthesis method of the compound Sub 1-1above, whereby a compound Sub 1-34 was obtained in an amount of 49.1 gin 63% yield.

8. Synthesis of 1-35

(1) Synthesis of Sub 1-I-35

The compound Sub 1-I-35 was synthesized by using phenanthren-9-ylboronicacid (70 g, 315.2 mmol), THF (1388 ml), 4-bromo-1-iodo-2-nitrobenzene(155.1 g, 472.9 mmol), Pd(PPh₃)₄ (18.2 g, 15.8 mmol), K₂CO₃ (130.7 g,945.7 mmol) and water (694 ml) in the same manner as described in thesynthesis method of the compound Sub 1-I-1 above, whereby a compound Sub1-I-35 was obtained in an amount of 85.8 g in 72% yield.

(2) Synthesis of Sub 1-II-35

The compound Sub 1-II-35 was synthesized by using Sub 1-I-35 (85.8 g,226.9 mmol), o-dichlorobenzene (930 ml) and triphenylphosphine (148.8 g,567.1 mmol) in the same manner as described in the synthesis method ofthe compound Sub 1-II-1 above, whereby a compound Sub 1-II-35 wasobtained in an amount of 60.5 g in 77% yield.

(3) Synthesis of Sub 1-III-35

The compound Sub 1-III-35 was synthesized by using Sub 1-II-35 (60.5 g,174.7 mmol), nitrobenzene (350 ml), 3-iodo-9,9-diphenyl-9H-fluorene(116.5 g, 262.1 mmol), Na₂SO₄ (24.8 g, 174.7 mmol), K₂CO₃ (24.2 g, 174.7mmol) and Cu (3.33 g, 52.4 mmol) in the same manner as described in thesynthesis method of the compound Sub 1-III-1 above, whereby a compoundSub 1-III-35 was obtained in an amount of 84.5 g in 73% yield.

(4) Synthesis of Sub 1-IV-35

The compound Sub 1-IV-35 was synthesized by using Sub 1-III-35 (84.5 g,127.5 mmol), DMF (854 ml), Bis(pinacolato)diboron (35.6 g, 140.3 mmol),Pd(dppf)Cl₂ (3.12 g, 3.82 mmol) and KOAc (37.5 g, 382.5 mmol) in thesame manner as described in the synthesis method of the compound Sub1-IV-1 above, whereby a compound Sub 1-IV-35 was obtained in an amountof 70.6 g in 78% yield. (5) Synthesis of Sub 1-35

The compound Sub 1-IV-35 (70.6 g, 99.5 mmol), THF (438 ml),1-bromo-2-iodobenzene (42.2 g, 149.2 mmol), Pd(PPh₃)₄ (5.75 g, 4.97mmol), K₂CO₃ (41.2 g, 298.4 mmol) and water (219 ml) in the same manneras described in the synthesis method of the compound Sub 1-1 above,whereby a compound Sub 1-35 was obtained in an amount of 45.6 g in 62%yield.

9. Synthesis of Sub 1-44

(1) Synthesis of Sub 1-III-44

The compound Sub 1-III-44 was synthesized by using Sub 1-II-1 (60 g, 244mmol), nitrobenzene (487 ml), 2-iododibenzo[b,d]furan (107.6 g, 365.7mmol), Na₂SO₄ (34.6 g, 244 mmol), K₂CO₃ (33.7 g, 244 mmol) and Cu (4.65g, 73.1 mmol) in the same manner as described in the synthesis method ofthe compound Sub 1-III-1 above, whereby a compound Sub 1-III-44 wasobtained in an amount of 68.4 g in 68% yield.

(2) Synthesis of Sub 1-IV-44

The compound Sub 1-IV-44 was synthesized by using Sub 1-III-44 (68.4 g,166 mmol), DMF (1045 ml), Bis(pinacolato)diboron (46.3 g, 182.5 mmol),Pd(dppf)Cl₂ (4.06 g, 5 mmol) and KOAc (48.8 g, 497.7 mmol) in the samemanner as described in the synthesis method of the compound Sub 1-IV-1above, whereby a compound Sub 1-IV-44 was obtained in an amount of 56.4g in 74% yield.

(3) Synthesis of Sub 1-44

The compound Sub 1-44 was synthesized by using Sub 1-IV-44 (56.4 g,122.8 mmol), THF (540 ml), 1-bromo-2-iodobenzene (52.1 g, 184 mmol),Pd(PPh₃)₄ (7.1 g, 6.14 mmol), K₂CO₃ (50.9 g, 368.4 mmol) and water (270ml) in the same manner as described in the synthesis method of thecompound Sub 1-1 above, whereby a compound Sub 1-44 was obtained in anamount of 17.9 g in 65% yield.

10. Synthesis of Sub 1-54

(1) Synthesis of Sub 1-III-54

The compound Sub 1-III-54 was synthesized by using Sub 1-II-1 (50 g,203.2 mmol), nitrobenzene (406 ml), 4-iodo-1,1′-biphenyl (85.4 g, 304.7mmol), Na₂SO₄ (28.9 g, 203.2 mmol), K₂CO₃ (28.1 g, 203.2 mmol) and Cu(3.87 g, 61 mmol) in the same manner as described in the synthesismethod of the compound Sub 1-III-1 above, whereby a compound Sub1-III-54 was obtained in an amount of 54.2 g in 68% yield.

(2) Synthesis of Sub 1-IV-54

The compound Sub 1-IV-54 was synthesized by using Sub 1-III-54 (54.2 g,136.1 mmol), DMF (857 ml), Bis(pinacolato)diboron (38.0 g, 150 mmol),Pd(dppf)Cl₂ (3.33 g, 4.1 mmol) and KOAc (40.1 g, 408 mmol) in the samemanner as described in the synthesis method of the compound Sub 1-IV-1above, whereby a compound Sub 1-IV-54 was obtained in an amount of 42.4g in 70% yield.

(3) Synthesis of Sub 1-54

The compound Sub 1-54 was synthesized by using Sub 1-IV-54 (42.4 g, 95.2mmol), THF (418 ml), 1-bromo-3-iodobenzene (40.4 g, 142.8 mmol),Pd(PPh₃)₄ (5.5 g, 4.76 mmol), K₂CO₃ (39.5 g, 285.6 mmol) and water (209ml) in the same manner as described in the synthesis method of thecompound Sub 1-1 above, whereby a compound Sub 1-54 was obtained in anamount of 30.7 g in 68% yield.

11. Synthesis of Sub 1-66

(1) Synthesis of Sub 1-III-66

The compound Sub 1-III-66 was synthesized by using Sub 1-II-1 (50 g,203.2 mmol), nitrobenzene (406 ml), 1-iodo-9,9-diphenyl-9H-fluorene(135.4 g, 305 mmol), Na₂SO₄ (28.9 g, 203.2 mmol), K₂CO₃ (28.1 g, 203.2mmol) and Cu (3.87 g, 61 mmol) in the same manner as described in thesynthesis method of the compound Sub 1-III-1 above, whereby a compoundSub 1-III-66 was obtained in an amount of 70.9 g in 62% yield.

(2) Synthesis of Sub 1-IV-66

The compound Sub 1-IV-66 was synthesized by using Sub 1-III-66 (70.9 g,126 mmol), DMF (794 ml), Bis(pinacolato)diboron (35.2 g, 138.7 mmol),Pd(dppf)Cl₂ (3.09 g, 3.78 mmol) and KOAc (37.11 g, 378.1 mmol) in thesame manner as described in the synthesis method of the compound Sub1-IV-1 above, whereby a compound Sub 1-IV-66 was obtained in an amountof 51.5 g in 67% yield.

(3) Synthesis of Sub 1-66

The compound Sub Sub 1-66 was synthesized by using Sub 1-IV-66 (51.5 g,84.5 mmol), THF (370 ml), 1-bromo-3-iodobenzene (35.8 g, 126.7 mmol),Pd(PPh₃)₄ (4.88 g, 4.22 mmol), K₂CO₃ (35.03 g, 253.5 mmol) and water(185 ml) in the same manner as described in the synthesis method of thecompound Sub 1-1 above, whereby a compound Sub Sub 1-66 was obtained inan amount of 33.5 g in 62% yield.

12. Synthesis of Sub 1-103

The compound Sub 1-103 was synthesized by Sub 1-IV-1 (31.2 g, 84.5mmol), THF (370 mL), 3-bromo-5-iodo-1,1′-biphenyl (46.8 g, 126.7 mmol),Pd(PPh₃)₄ (4.88 g, 4.22 mmol), K₂CO₃ (35.03 g, 253.5 mmol) and water(185 mL) in the same manner as described in the synthesis method of thecompound Sub 1-1 above, whereby a compound Sub 1-103 was obtained in anamount of 26.1 g in 65% yield.

13. Synthesis of Sub 1-115

The compound Sub 1-115 was synthesized by Sub 1-IV-1 (31.2 g, 84.5mmol), THF (370 mL), 3-bromo-5-iodo-1,1′-biphenyl (46.8 g, 126.7 mmol),Pd(PPh₃)₄ (4.88 g, 4.22 mmol), K₂CO₃ (35.03 g, 253.5 mmol) and water(185 mL) in the same manner as described in the synthesis method of thecompound Sub 1-1 above, whereby a compound Sub 1-115 was obtained in anamount of 24.5 g in 61% yield.

Examples of Sub 1 compounds include, but are not limited to, thefollowing compounds, and FD-MS(Field Desorption-Mass Spectrometry) dataof the compounds are given in Table 1 below.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1-1 m/z = 397.05(C₂₄H₁₆BrN =398.29) Sub 1-2 m/z = 447.06(C₂₈H₁₈BrN = 448.35) Sub 1-3 m/z =473.08(C₃₀H₂₀BrN = 474.39) Sub 1-4 m/z = 447.06(C₂₈H₁₈BrN = 448.35) Sub1-5 m/z = 473.08(C₃₀H₂₀BrN = 474.39) Sub 1-6 m/z = 473.08(C₃₀H₂₀BrN =474.39) Sub 1-7 m/z = 579.07(C₃₆H₂₂BrNS = 580.54) Sub 1-8 m/z =476.06(C₂₇H₁₇BrN₄ = 477.35) Sub 1-9 m/z = 437.08(C₂₇H₂₀BrN = 438.36) Sub1-10 m/z = 600.12(C₃₉H₂₅BrN₂ = 601.53) Sub 1-11 m/z = 473.08(C₃₀H₂₀BrN =474.39) Sub 1-12 m/z = 601.12(C₃₈H₂₄BrN₃ = 602.52) Sub 1-13 m/z =637.14(C₄₃H₂₈BrN = 638.59) Sub 1-14 m/z = 637.14(C₄₃H₂₈BrN = 638.59) Sub1-15 m/z = 637.14(C₄₃H₂₈BrN = 638.59) Sub 1-16 m/z = 637.14(C₄₃H₂₈BrN =638.59) Sub 1-17 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub 1-18 m/z =549.11(C₃₆H₂₄BrN = 550.49) Sub 1-19 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub1-20 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub 1-21 m/z = 549.11(C₃₆H₂₄BrN =550.49) Sub 1-22 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub 1-23 m/z =549.11(C₃₆H₂₄BrN = 550.49) Sub 1-24 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub1-25 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub 1-26 m/z = 549.11(C₃₆H₂₄BrN =550.49) Sub 1-27 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub 1-28 m/z =549.11(C₃₆H₂₄BrN = 550.49) Sub 1-29 m/z = 559.2(C₃₆H₁₄D₁₀BrN = 560.6)Sub 1-30 m/z = 559.17(C₃₆H₁₄D₁₀BrN = 560.6) Sub 1-31 m/z =554.1(C₃₆H₁₉D₅BrN = 555.52) Sub 1-32 m/z = 687.16(C₄₇H₃₀BrN = 688.65)Sub 1-33 m/z = 687.16(C₄₇H₃₀BrN = 688.65) Sub 1-34 m/z =687.16(C₄₇H₃₀BrN = 688.65) Sub 1-35 m/z = 737.17(C₅₁H₃₂BrN = 738.71) Sub1-36 m/z = 737.17(C₅₁H₃₂BrN = 738.71) Sub 1-37 m/z = 687.16(C₄₇H₃₀BrN =688.65) Sub 1-38 m/z = 737.17(C₅₁H₃₂BrN = 738.71) Sub 1-39 m/z =737.17(C₅₁H₃₂BrN = 738.71) Sub 1-40 m/z = 503.03(C₃₀H₁₈BrNS = 504.44)Sub 1-41 m/z = 503.03(C₃₀H₁₈BrNS = 504.44) Sub 1-42 m/z =503.03(C₃₀H₁₈BrNS = 504.44) Sub 1-43 m/z = 503.03(C₃₀H₁₈BrNS = 504.44)Sub 1-44 m/z = 487.06(C₃₀H₁₈BrNO = 488.37) Sub 1-45 m/z =487.1(C₃₀H₁₈BrNO = 488.37) Sub 1-46 m/z = 487.06(C₃₀H₁₈BrNO = 488.37)Sub 1-47 m/z = 487.1(C₃₀H₁₈BrNO = 488.37) Sub 1-48 m/z =737.17(C₅₁H₃₂BrN = 738.71) Sub 1-49 m/z = 737.17(C₅₁H₃₂BrN = 738.71) Sub1-50 m/z = 553.05(C₃₄H₂₀BrNS = 554.50) Sub 1-51 m/z = 537.07(C₃₄H₂₀BrNO= 538.43) Sub 1-52 m/z = 397.05(C₂₄H₁₆BrN = 398.29) Sub 1-53 m/z =447.06(C₂₈H₁₈BrN = 448.35) Sub 1-54 m/z = 473.08(C₃₀H₂₀BrN = 474.39) Sub1-55 m/z = 447.06(C₂₈H₁₈BrN = 448.35) Sub 1-56 m/z = 473.08(C₃₀H₂₀BrN =474.39) Sub 1-57 m/z = 473.08(C₃₀H₂₀BrN = 474.39) Sub 1-58 m/z =579.07(C₃₆H₂₂BrNS = 580.54) Sub 1-59 m/z = 476.06(C₂₇H₁₇BrN₄ = 477.35)Sub 1-60 m/z = 437.08(C₂₇H₂₀BrN = 438.36) Sub 1-61 m/z =600.12(C₃₉H₂₅BrN₂ = 601.53) Sub 1-62 m/z = 473.08(C₃₀H₂₀BrN = 474.39)Sub 1-63 m/z = 601.12(C₃₈H₂₄BrN₃ = 602.52) Sub 1-64 m/z =637.14(C₄₃H₂₈BrN = 638.59) Sub 1-65 m/z = 637.14(C₄₃H₂₈BrN = 638.59) Sub1-66 m/z = 637.14(C₄₃H₂₈BrN = 638.59) Sub 1-67 m/z = 637.14(C₄₃H₂₈BrN =638.59) Sub 1-68 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub 1-69 m/z =549.11(C₃₆H₂₄BrN = 550.49) Sub 1-70 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub1-71 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub 1-72 m/z = 549.11(C₃₆H₂₄BrN =550.49) Sub 1-73 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub 1-74 m/z =549.11(C₃₆H₂₄BrN = 550.49) Sub 1-75 m/z = 549.11(C₃₆H2₂₄BrN = 550.49)Sub 1-76 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub 1-77 m/z =549.11(C₃₆H₂₄BrN = 550.49) Sub 1-78 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub1-79 m/z = 549.11(C₃₆H₂₄BrN = 550.49) Sub 1-80 m/z = 559.17(C₃₆H₁₄D₁₀BrN= 560.6) Sub 1-81 m/z = 559.2(C₃₆H₁₄D₁₀BrN = 560.6) Sub 1-82 m/z =554.14(C₃₆H₁₉D₅BrN = 555.52) Sub 1-83 m/z = 687.16(C₄₇H₃₀BrN = 688.65)Sub 1-84 m/z = 687.16(C₄₇H₃₀BrN = 688.65) Sub 1-85 m/z =687.16(C₄₇H₃₀BrN = 688.65) Sub 1-86 m/z = 737.17(C₅₁H₃₂BrN = 738.71) Sub1-87 m/z = 737.17(C₅₁H₃₂BrN = 738.71) Sub 1-88 m/z = 687.16(C₄₇H₃₀BrN =688.65) Sub 1-89 m/z = 737.17(C₅₁H₃₂BrN = 738.71) Sub 1-90 m/z =737.17(C₅₁H₃₂BrN = 738.71) Sub 1-91 m/z = 503.03(C₃₀H₁₈BrNS = 504.44)Sub 1-92 m/z = 503.03(C₃₀H₁₈BrNS = 504.44) Sub 1-93 m/z =503.03(C₃₀H₁₈BrNS = 504.44) Sub 1-94 m/z = 503.03(C₃₀H₁₈BrNS = 504.44)Sub 1-95 m/z = 487.1(C₃₀H₁₈BrNO = 488.37) Sub 1-96 m/z =487.06(C₃₀H₁₈BrNO = 488.37) Sub 1-97 m/z = 487.1(C₃₀H₁₈BrNO = 488.37)Sub 1-98 m/z = 487.06(C₃₀H₁₈BrNO = 488.37) Sub 1-99 m/z =737.17(C₅₁H₃₂BrN = 738.71) Sub 1-100 m/z = 737.17(C₅₁H₃₂BrN = 738.71)Sub 1-101 m/z = 553.05(C₃₄H₂₀BrNS = 554.50) Sub 1-102 m/z =537.07(C₃₄H₂₀BrNO = 538.43) Sub 1-103 m/z = 473.08(C30H20BrN = 474.39)Sub 1-104 m/z = 549.11(C36H24BrN = 550.49) Sub 1-105 m/z =549.11(C36H24BrN = 550.49) Sub 1-106 m/z = 599.12(C40H26BrN = 600.55)Sub 1-107 m/z = 599.12(C40H26BrN = 600.55) Sub 1-108 m/z =599.12(C40H26BrN = 600.55) Sub 1-109 m/z = 599.12(C40H26BrN = 600.55)Sub 1-110 m/z = 474.07(C29H19BrN2 = 475.38) Sub 1-111 m/z =524.09(C33H21BrN2 = 525.44) Sub 1-112 m/z = 525.08(C32H20BrN3 = 526.43)Sub 1-113 m/z = 475.07(C28H18BrN3 = 476.37) Sub 1-114 m/z =473.08(C30H20BrN = 474.39) Sub 1-115 m/z = 473.08(C30H20BrN = 474.39)Sub 1-116 m/z = 473.08(C30H20BrN = 474.39) Sub 1-117 m/z =523.09(C34H22BrN = 524.45) Sub 1-118 m/z = 523.09(C34H22BrN = 524.45)Sub 1-119 m/z = 549.11(C36H24BrN = 550.49) Sub 1-120 m/z =549.11(C36H24BrN = 550.49) Sub 1-121 m/z = 599.12(C40H26BrN = 600.55)Sub 1-122 m/z = 599.12(C40H26BrN = 600.55) Sub 1-123 m/z =599.12(C40H26BrN = 600.55) Sub 1-124 m/z = 599.12(C40H26BrN = 600.55)Sub 1-125 m/z = 474.07(C29H19BrN2 = 475.38) Sub 1-126 m/z =524.09(C33H21BrN2 = 525.44) Sub 1-127 m/z = 525.08(C32H20BrN3 = 526.43)Sub 1-128 m/z = 475.07(C28H18BrN3 = 476.37)

II. Synthesis Examples of Sub 2

Sub 2 of the Reaction Scheme 1 can be synthesized according to, but notlimited to, the following Reaction Scheme 48.

The synthesis examples of compounds included in Sub 2 are as below.

1. Synthesis of Sub 2-1

Bromobenzene (37.1 g, 236.2 mmol) was dissolved in toluene (2200 ml) ina round bottom flask. Then, aniline (20 g, 214.8 mmol), Pd₂(dba)₃ (9.83g, 10.7 mmol), P(t-Bu)₃ (4.34 g, 21.5 mmol) and NaOt-Bu (62 g, 644.3mmol) were added into the round bottom flask, and the mixture wasstirred 100° C. After the completion of the reaction, the reactionproduct was extracted with ether and water. The extracted organic layerwas dried over MgSO₄ and concentrated. The concentrated resultant wasseparated by silica gel column chromatography, and was thenrecrystallized, whereby a compound Sub 2-1 was obtained in an amount of28 g in 77% yield.

2. Synthesis of Sub 2-3

The compound Sub 2-3 was synthesized by using 3-bromo-1,1′-biphenyl(55.1 g, 236.2 mmol), aniline (20 g, 214.8 mmol), Pd₂(dba)₃ (9.83 g,10.7 mmol), P(t-Bu)₃ (4.34 g, 21.5 mmol), NaOt-Bu (62 g, 644.3 mmol) andtoluene (2200 ml) in the same manner as described in the synthesismethod of the compound Sub 2-1 above, whereby a compound Sub 2-3 wasobtained in an amount of 41.1 g in 78% yield.

3. Synthesis of Sub 2-4

The compound Sub 2-4 was synthesized by using 4-bromo-1,1′-biphenyl(37.88 g, 162.5 mmol), [1,1′-biphenyl]-4-amine (25 g, 147.7 mmol),Pd₂(dba)₃ (6.76 g, 7.4 mmol), P(t-Bu)₃ (3 g, 14.8 mmol) and NaOt-Bu(66.62 g, 693.2 mmol) in the same manner as described in the synthesismethod of the compound Sub 2-1 above, whereby a compound Sub 2-4 wasobtained in an amount of 35.6 g in 75% yield.

4. Synthesis of Sub 2-7

The compound Sub 2-7 was synthesized by using 2-bromonaphthalene (39.8g, 192.1 mmol), naphthalen-1-amine (25 g, 174.6 mmol), Pd₂(dba)₃ (8.0 g,8.73 mmol), P(t-Bu)₃ (3.53 g, 17.5 mmol), NaOt-Bu (50.3 g, 523.8 mmol)and toluene (1800 ml) in the same manner as described in the synthesismethod of the compound Sub 2-1 above, whereby a compound Sub 2-7 wasobtained in an amount of 36.2 g in 77% yield.

5. Synthesis of Sub 2-9

The compound Sub 2-9 was synthesized by using2-bromo-9,9-diphenyl-9H-fluorene (93.9 g, 236.2 mmol), toluene (2250ml), aniline (20 g, 214.8 mmol), Pd₂(dba)₃ (9.83 g, 10.7 mmol), P(t-Bu)₃(4.34 g, 21.5 mmol) and NaOt-Bu (62 g, 644.3 mmol) in the same manner asdescribed in the synthesis method of the compound Sub 2-1 above, wherebya compound Sub 2-9 was obtained in an amount of 63.3 g in 72% yield.

6. Synthesis of Sub 2-12

The compound Sub 2-12 was synthesized by using2-bromo-9,9-diphenyl-9H-fluorene (64.6 g, 162.5 mmol), toluene(1550 ml),[1,1′-biphenyl]-4-amine (25 g, 147.7 mmol), Pd₂(dba)₃ (6.76 g, 162.5mmol), P(t-Bu)₃ (3 g, 14.8 mmol) and NaOt-Bu (42.6 g, 443.2 mmol) in thesame manner as described in the synthesis method of the compound Sub 2-1above, whereby a compound Sub 2-12 was obtained in an amount of 53.8 gin 75% yield. 7. Synthesis of Sub 2-13

The compound Sub 2-13 was synthesized by using3-bromodibenzo[b,d]thiophene (42.8 g, 162.5 mmol), toluene (1550 ml),[1,1′-biphenyl]-4-amine (25 g, 147.7 mmol), Pd₂(dba)₃ (6.76 g, 162.5mmol), P(t-Bu)₃ (3 g, 14.8 mmol) and NaOt-Bu (42.6 g, 443.2 mmol) in thesame manner as described in the synthesis method of the compound Sub 2-1above, whereby a compound Sub 2-13 was obtained in an amount of 37.9 gin 73% yield.

8. Synthesis of Sub 2-17

The compound Sub 2-17 was synthesized by using 1-bromo-4-methoxybenzene(36 g, 192.1 mmol), naphthalen-1-amine (25 g, 174.6 mmol), Pd₂(dba)₃(8.0 g, 8.73 mmol), P(t-Bu)₃ (3.53 g, 17.5 mmol), NaOt-Bu (50.3 g, 523.8mmol) and toluene (1800 ml) in the same manner as described in thesynthesis method of the compound Sub 2-1 above, whereby a compound Sub2-17 was obtained in an amount of 32.2 g in 74% yield.

9. Synthesis of Sub 2-26

The compound Sub 2-26 was synthesized by using5′-bromo-1,1′:3′,1″-terphenyl (73.04 g, 236.2 mmol), amine (20 g, 214.8mmol), Pd₂(dba)₃ (9.83 g, 10.7 mmol), P(t-Bu)₃ (4.34 g, 21.5 mmol),NaOt-Bu (62 g, 644.3 mmol) and toluene (2250 ml) in the same manner asdescribed in the synthesis method of the compound Sub 2-1 above, wherebya compound Sub 2-26 was obtained in an amount of 49 g in 71% yield.

10. Synthesis of Sub 2-31

The compound Sub 2-31 was synthesized by 2-bromo-9-phenyl-9H-carbazole(52.4 g, 162.5 mmol), toluene(1550 mL), [1,1′-biphenyl]-4-amine (25 g,147.7 mmol), Pd₂(dba)₃ (6.76 g, 162.5 mmol), P(t-Bu)₃ (3 g, 14.8 mmol)and NaOt-Bu (42.6 g, 443.2 mmol) in the same manner as described in thesynthesis method of the compound Sub 2-1 above, whereby a compound Sub2-26 was obtained in an amount of 45.4 g in 68% yield.

Examples of Sub 2 compounds include, but are not limited to, thefollowing compounds, and FD-MS data of the compounds are given in Table2 below.

 2 Compound FD-MS compound FD-MS Sub 2-1 m/z = 169.09(C₁₂H₁₁N = 169.22)Sub 2-2 m/z = 245.12(C₁₈H₁₅N = 245.32) Sub 2-3 m/z = 245.12(C₁₈H₁₅N =245.32) Sub 2-4 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-5 m/z =321.15(C₂₄H₁₉N = 321.41) Sub 2-6 m/z = 269.12(C₂₀H₁₅N = 269.34) Sub 2-7m/z = 269.12(C₂₀H₁₅N = 269.34) Sub 2-8 m/z = 295.14(C₂₂H₁₇N = 295.38)Sub 2-9 m/z = 409.18(C₃₁H₂₃N = 409.52) Sub 2-10 m/z = 483.20(C₃₇H₂₅N =483.60) Sub 2-11 m/z = 459.20(C₃₅H₂₅N = 459.58) Sub 2-12 m/z =485.21(C₃₇H₂₇N = 485.62) Sub 2-13 m/z = 351.11(C₃₄H₁₇NS = 351.46) Sub2-14 m/z = 335.13(C₂₄H₁₇NO = 335.40) Sub 2-15 m/z = 297.13(C₂₀H₁₅N₃ =297.35) Sub 2-16 m/z = 219.10(C₁₆H₁₃N = 219.28) Sub 2-17 m/z =249.12(C₁₇H₁₅NO = 249.31) Sub 2-18 m/z = 197.12(C₁₄H₁₅N = 197.28) Sub2-19 m/z = 229.11(C₁₄H₁₅NO₂ = 229.27) Sub 2-20 m/z = 174.12(C₁₂H₆D₅N =174.25) Sub 2-21 m/z = 281.21(C₂₀H₂₇N = 281.44) Sub 2-22 m/z =321.15(C₂₄H₁₉N = 321.41) Sub 2-23 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub2-24 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-25 m/z = 321.15(C₂₄H₁₉N =321.41) Sub 2-26 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 2-27 m/z =297.13(C₂₀H₁₅N₃ = 297.35) Sub 2-28 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub2-29 m/z = 361.18(C₂₇H₂₃N = 361.48) Sub 2-30 m/z = 499.20(C₃₆H₂₅N₃ =499.60) Sub 2-31 m/z = 499.20(C₃₆H₂₂N₂ = 410.51) Sub 2-32 m/z =424.16(C₃₀H₂₀N₂O = 424.49) Sub 2-33 m/z = 440.13(C₃₀H₂₀N₂S = 440.56) Sub2-34 m/z = 384.16(C₂₈H₂₀N₂ = 384.47) Sub 2-35 m/z = 334.15(C₂₄H₁₈N₂ =334.41) Sub 2-36 m/z = 450.21(C₃₃H₂₆N₂ = 450.57) Sub 2-37 m/z =410.18(C₃₀H₂₂N₂ = 410.51) Sub 2-38 m/z = 410.18(C₃₀H₂₂N₂ = 410.51) Sub2-39 m/z = 575.24(C₄₂H₂₉N₃ = 575.70) Sub 2-40 m/z = 574.24(C₄₃H₃₀N₂ =574.71) Sub 2-41 m/z = 460.19(C₃₄H₂₄N₂ = 460.57) Sub 2-42 m/z =460.19(C₃₄H₂₄N₂ = 460.57) Sub 2-43 m/z = 461.19(C₃₃H₂₃N₃ = 461.56) Sub2-44 m/z = 626.27(C₄₇H₃₄N₂ = 626.79) Sub 2-45 m/z = 565.23(C₃₉H₂₇N₅ =565.67) Sub 2-46 m/z = 415.21(C₃₀H₁₇D₅N₂ = 415.54) Sub 2-47 m/z =486.21(C₃₆H₂₆N₂ = 486.61) Sub 2-48 m/z = 415.21(C₃₀H₁₇D₅N₂ = 415.54)

III. Synthesis Examples of Final Products

Sub 2 (1 eq) was dissolved in toluene in a round bottom flask. Then, 1(1.1 eq), Pd₂(dba)₃ (0.05 eq), P(t-Bu)₃ (0.1 eq) and NaOt-Bu (3 eq) wereadded into the round bottom flask, and the mixture was stirred 100° C.After the completion of the reaction, the reaction product was extractedwith CH₂Cl₂ and water. The extracted organic layer was dried over MgSO₄and concentrated. The concentrated resultant was separated by silica gelcolumn chromatography, and was then recrystallized, whereby Finalproducts was obtained.

1. Synthesis of Product P1-1

Sub 2-1 (8 g, 47.3 mmol) was dissolved in in toluene (500 ml) in a roundbottom flask. Then, Sub 1-1 (20.7 g, 52.0 mmol), Pd₂(dba)₃ (2.2 g, 2.4mmol), P(t-Bu)₃ (1 g, 4.73 mmol) and NaOt-Bu (13.6 g, 141.8 mmol) wereadded into the round bottom flask, and the mixture was stirred at 100°C. After the completion of the reaction, the reaction product wasextracted with CH₂Cl₂ and water. The extracted organic layer was driedover MgSO₄ and concentrated. The concentrated resultant was separated bysilica gel column chromatography, and was then recrystallized, whereby acompound P1-1 was obtained in an amount of 16.2 g in 70% yield.

2. Synthesis of Product P1-4

The compound P1-4 was synthesized by using Sub 2-4 (7.8 g, 24.9 mmol),Sub 1-1 (10.7 g, 27.4 mmol), Pd₂(dba)₃ (1.14 g, 1.24 mmol), P(t-Bu)₃(0.5 g, 2.49 mmol), NaOt-Bu (7.17 g, 74.7 mmol) and toluene (265 ml) inthe same manner as described in the synthesis method of the compoundProduct P1-1 above, whereby a compound P1-4 was obtained in an amount of10.6 g in 68% yield.

3. Synthesis of Product P1-8

The compound P1-8 was synthesized by using Sub 2-9 (10 g, 24.4 mmol),Sub 2-9 (10 g, 24.4 mmol), Sub 1-1 (10.7 g, 27.4 mmol), Pd₂(dba)₃ (1.14g, 1.24 mmol), P(t-Bu)₃ (0.5 g, 2.49 mmol), NaOt-Bu (7.17 g, 74.7 mmol)and toluene (265 ml) in the same manner as described in the synthesismethod of the compound Product P1-1 above, whereby a compound P1-8 wasobtained in an amount of 11.5 g in 77% yield.

4. Synthesis of Product P1-17

The compound P1-17 was synthesized by using Sub 2-13 (10.0 g, 28.5mmol), Sub 1-4 (14.0 g, 31.3 mmol), Pd₂(dba)₃ (1.3 g, 1.42 mmol),P(t-Bu)₃ (0.6 g, 2.85 mmol), NaOt-Bu (8.2 g, 85.4 mmol) and toluene (300ml) in the same manner as described in the synthesis method of thecompound Product P1-1 above, whereby a compound P1-17 was obtained in anamount of 13.5 g in 66% yield.

5. Synthesis of Product P1-49

The compound P2-49 was synthesized by using Sub 2-6 (11.0 g, 37.13mmol), Sub 1-65 (23.7 g, 40.84 mmol), Pd₂(dba)₃ (1.7 g, 1.9 mmol),P(t-Bu)₃ (0.8 g, 3.7 mmol), NaOt-Bu (10.7 g, 111.4 mmol) and toluene(390 ml) in the same manner as described in the synthesis method of thecompound Product P1-1 above, whereby a compound P2-49 was obtained in anamount of 24.7 g in 73% yield.

6. Synthesis of Product P2-77

The compound P2-77 was synthesized by using Sub 2-1 (8.0 g, 47.3 mmol),Sub 1-68 (28.6 g, 52 mmol), Pd₂(dba)₃ (2.2 g, 2.4 mmol), P(t-Bu)₃ (1 g,4.73 mmol), NaOt-Bu (13.6 g, 141.8 mmol) and toluene (500 ml) in thesame manner as described in the synthesis method of the compound ProductP1-1 above, whereby a compound P2-77 was obtained in an amount of 22.7 gin 75% yield.

7. Synthesis of Product P3-2

The compound P3-4 was synthesized by Sub 2-28 (22.4 g, 47.3 mmol), Sub1-103 (14.3 g, 52 mmol), Pd₂(dba)₃ (2.2 g, 2.4 mmol), P(t-Bu)₃ (1 g,4.73 mmol), NaOt-Bu (13.6 g, 141.8 mmol) and toluene (500 mL) in thesame manner as described in the synthesis method of the compound ProductP1-1 above, whereby a compound P3-2 was obtained in an amount of 23.1 gin 73% yield.

8. Synthesis of Product P3-22

The compound P3-22 was synthesized by using Sub 2-29 (22.4 g, 47.3mmol), Sub 1-121 (18.8 g, 52 mmol), Pd₂(dba)₃ (2.2 g, 2.4 mmol),P(t-Bu)₃ (1 g, 4.73 mmol), NaOt-Bu (13.6 g, 141.8 mmol) and toluene (500mL) in the same manner as described in the synthesis method of thecompound Product P1-1 above, whereby a compound P3-22 was obtained in anamount of 24.3 g in 68% yield.

9. Synthesis of Product P4-2

The compound P4-2 was synthesized by using Sub 2-31 (19.4 g, 47.3 mmol),Sub 1-1 (20.7 g, 52 mmol), Pd₂(dba)₃ (2.2 g, 2.4 mmol), P(t-Bu)₃ (1 g,4.73 mmol), NaOt-Bu (13.6 g, 141.8 mmol) and toluene (500 mL) in thesame manner as described in the synthesis method of the compound ProductP1-1 above, whereby a compound P4-2 was obtained in an amount of 30.3 gin 80% yield.

10. Synthesis of Product P4-9

The compound P4-9 was synthesized by using Sub 2-36 (21.3, 47.3 mmol),Sub 1-1 (20.7 g, 52 mmol), Pd₂(dba)₃ (2.2 g, 2.4 mmol), P(t-Bu)₃ (1 g,4.73 mmol), NaOt-Bu (13.6 g, 141.8 mmol) and toluene (500 mL) in thesame manner as described in the synthesis method of the compound ProductP1-1 above, whereby a compound P4-9 was obtained in an amount of 32.7 gin 82% yield.

11. Synthesis of Product P4-15

The compound P4-15 was synthesized by using Sub 2-33 (20.8 g, 47.3mmol), Sub 1-129 (24.7 g, 52 mmol), Pd₂(dba)₃ (2.2 g, 2.4 mmol),P(t-Bu)₃ (1 g, 4.73 mmol), NaOt-Bu (13.6 g, 141.8 mmol) and toluene (500mL) in the same manner as described in the synthesis method of thecompound Product P1-1 above, whereby a compound P4-15 was obtained in anamount of 33.8 g in 78% yield.

12. Synthesis of Product P4-20

The compound P4-20 was synthesized by using Sub 2-35 (15.8 g, 47.3mmol), Sub 1-130 (26.8 g, 52 mmol), Pd₂(dba)₃ (2.2 g, 2.4 mmol),P(t-Bu)₃ (1 g, 4.73 mmol), NaOt-Bu (13.6 g, 141.8 mmol) and toluene (500mL) in the same manner as described in the synthesis method of thecompound Product P1-1 above, whereby a compound P4-20 was obtained in anamount of 32.3 g in 81% yield.

13. Synthesis of Product P4-29

The compound P4-29 was synthesized by using Sub 2-41 (21.8 g, 47.3mmol), Sub 1-56 (20.7 g, 52 mmol), Pd₂(dba)₃ (2.2 g, 2.4 mmol), P(t-Bu)₃(1 g, 4.73 mmol), NaOt-Bu (13.6 g, 141.8 mmol) and toluene (500 mL) inthe same manner as described in the synthesis method of the compoundProduct P1-1 above, whereby a compound P4-29 was obtained in an amountof 32.0 g in 79% yield.

14. Synthesis of Product P4-33

The compound P4-33 was synthesized by using Sub 2-45 (26.8 g, 47.3mmol), Sub 1-56 (20.7 g, 52 mmol), Pd₂(dba)₃ (2.2 g, 2.4 mmol), P(t-Bu)₃(1 g, 4.73 mmol), NaOt-Bu (13.6 g, 141.8 mmol) and toluene (500 mL) inthe same manner as described in the synthesis method of the compoundProduct P1-1 above, whereby a compound P4-33 was obtained in an amountof 36.7 g in 80% yield.

15. Synthesis of Product P4-36

The compound P4-36 was synthesized by using Sub 2-48 (19.7 g, 47.3mmol), Sub 1-56 (20.7 g, 52 mmol), Pd₂(dba)₃ (2.2 g, 2.4 mmol), P(t-Bu)₃(1 g, 4.73 mmol), NaOt-Bu (13.6 g, 141.8 mmol) and toluene (500 mL) inthe same manner as described in the synthesis method of the compoundProduct P1-1 above, whereby a compound P4-36 was obtained in an amountof 29.0 g in 76% yield.

FD-MS data of the final products, P1-1 to P1-112, P2-1 to P2-112, P3-1to P3-38, and P4-1 to P4-36, synthesized according to the abovesynthesis example are given in Table 3 below.

TABLE 3 Compound FD-MS compound FD-MS P1-1 m/z = 486.21(C₃₆H₂₆N₂ =486.61) P1-2 m/z = 562.24(C₄₂H₃₀N₂ = 562.70) P1-3 m/z = 562.24(C₄₂H₃₀N₂= 562.70) P1-4 m/z = 638.27(C₄₈H₃₄N₂ = 638.80) P1-5 m/z =586.24(C₄₄H₃₀N₂ = 586.72) P1-6 m/z = 586.24(C₄₄H₃₀N₂ = 586.72) P1-7 m/z= 612.26(C₄₆H₃₂N₂ = 612.76) P1-8 m/z = 726.30(C₅₅H₃₈N₂ = 726.90) P1-9m/z = 638.27(C₄₈H₃₄N₂ = 638.80) P1-10 m/z = 800.32(C₆₁H₄₀N₂ = 800.98)P1-11 m/z = 536.23(C₄₀H₂₈N₂ = 536.66) P1-12 m/z = 688.29(C₅₂H₃₆N₂ =688.86) P1-13 m/z = 852.35(C₆₅H₄₄N₂ = 853.06) P1-14 m/z =638.27(C₄₈H₃₄N₂ = 638.80) P1-15 m/z = 688.29(C₅₂H₃₆N₂ = 688.86) P1-16m/z = 662.27(C₅₀H₃₄N₂ = 662.82) P1-17 m/z = 718.24(C₅₂H₃₄N₂S = 718.90)P1-18 m/z = 702.27(C₅₂H₃₄N₂O = 702.84) P1-19 m/z = 664.26(C₄₈H₃₂N₄ =664.79) P1-20 m/z = 664.26(C₄₈H₃₂N₄ = 664.79) P1-21 m/z =562.24(C₄₂H₃₀N₂ = 562.70) P1-22 m/z = 562.24(C₄₂H₃₀N₂ = 562.70) P1-23m/z = 780.35(C₅₆H₄₈N₂S = 781.06) P1-24 m/z = 665.26(C₄₇H₃₁N₅ = 665.78)P1-25 m/z = 526.24(C₃₉H₃₀N₂ = 526.67) P1-26 m/z = 739.30(C₅₅H₃₇N₃ =739.90) P1-27 m/z = 642.27(C₄₇H₃₄N₂O = 642.79) P1-28 m/z =790.31(C₅₈H₃₈N₄ = 790.95) P1-29 m/z = 726.30(C₅₅H₃₈N₂ = 726.90) P1-30m/z = 802.33(C₆₁H₄₂N₂ = 803.00) P1-31 m/z = 802.33(C₆₁H₄₂N₂ = 803.00)P1-32 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-33 m/z = 726.30(C₅₅H₃₈N₂ =726.90) P1-34 m/z = 726.30(C₅₅H₃₈N₂ = 726.90) P1-35 m/z =852.35(C₆₅H₄₄N₂ = 853.06) P1-36 m/z = 1016.41(C₇₈H₅₂N₂ = 1017.26) P1-37m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-38 m/z = 1040.41(C₈₀H₅₂N₂ = 1041.28)P1-39 m/z = 776.32(C₅₉H₄₀N₂ = 776.96) P1-40 m/z = 878.37(C₆₇H₄₆N₂ =879.10) P1-41 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-42 m/z =878.37(C₆₇H₄₆N₂ = 879.10) P1-43 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-44m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-45 m/z = 726.30(C₅₅H₃₈N₂ = 726.90)P1-46 m/z = 802.33(C₆₁H₄₂N₂ = 803.00) P1-47 m/z = 802.33(C₆₁H₄₂N₂ =803.00) P1-48 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-49 m/z =826.33(C₆₃H₄₂N₂ = 827.02) P1-50 m/z = 826.33(C₆₃H₄₂N₂ = 827.02) P1-51m/z = 852.35(C₆₅H₄₄N₂ = 853.06) P1-52 m/z = 1016.41(C₇₈H₅₂N₂ = 1017.26)P1-53 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-54 m/z = 1040.41(C₈₀H₅₂N₂ =1041.28) P1-55 m/z = 776.32(C₅₉H₄₀N₂ = 776.96) P1-56 m/z =878.37(C₆₇H₄₆N₂ = 879.10) P1-57 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-58m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-59 m/z = 878.37(C₆₇H₄₆N₂ = 879.10)P1-60 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-61 m/z = 726.30(C₅₅H₃₈N₂ =726.90) P1-62 m/z = 802.33(C₆₁H₄₂N₂ = 803.00) P1-63 m/z =802.33(C₆₁H₄₂N₂ = 803.00) P1-64 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-65m/z = 826.33(C₆₃H₄₂N₂ = 827.02) P1-66 m/z = 826.33(C₆₃H₄₂N₂ = 827.02)P1-67 m/z = 852.35(C₆₅H₄₄N₂ = 853.06) P1-68 m/z = 1016.41(C₇₈H₅₂N₂ =1017.26) P1-69 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-70 m/z =1040.41(C₈₀H₅₂N₂ = 1041.28) P1-71 m/z = 776.32(C₅₉H₄₀N₂ = 776.96) P1-72m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-73 m/z = 878.37(C₆₇H₄₆N₂ = 879.10)P1-74 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-75 m/z = 878.37(C₆₇H₄₆N₂ =879.10) P1-76 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P1-77 m/z =638.27(C₄₈H₃₄N₂ = 638.80) P1-78 m/z = 714.30(C₅₄H₃₈N₂ = 714.89) P1-79m/z = 714.30(C₅₄H₃₈N₂ = 714.89) P1-80 m/z = 790.33(C₆₀H₄₂N₂ = 790.99)P1-81 m/z = 738.30(C₅₆H₃₈N₂ = 738.91) P1-82 m/z = 738.30(C₅₆H₃₈N₂ =738.91) P1-83 m/z = 764.32(C₅₈H₄₀N₂ = 764.95) P1-84 m/z =928.38(C₇₁H₄₈N₂ = 929.15) P1-85 m/z = 790.33(C₆₀H₄₂N₂ = 790.99) P1-86m/z = 638.27(C₄₈H₃₄N₂ = 638.80) P1-87 m/z = 638.27(C₄₈H₃₄N₂ = 638.80))P1-88 m/z = 638.27(C₄₈H₃₄N₂ = 638.80) P1-89 m/z = 648.33(C₄₈H₂₄D₁₀N₂ =648.86) P1-90 m/z = 724.37(C₅₄H₂₈D₁₀N₂ = 724.95) P1-91 m/z =795.37(C₆₀H₃₇D₅N₂ = 796.02) P1-92 m/z = 643.30(C₄₈H₂₉D₅N₂ = 643.83)P1-93 m/z = 776.32(C₅₉H₄₀N₂ = 776.96) P1-94 m/z = 826.33(C₆₃H₄₂N₂ =827.02) P1-95 m/z = 776.32(C₅₉H₄₀N₂ = 776.96) P1-96 m/z =826.33(C₆₃H₄₂N₂ = 827.02) P1-97 m/z = 854.37(C₆₅H₄₆N₂ = 855.07) P1-98m/z = 836.34(C₆₁H₄₄N₂O₂ = 837.01) P1-99 m/z = 826.33(C₆₃H₄₂N₂ = 827.02)P1-100 m/z = 826.33(C₆₃H₄₂N₂ = 827.02) P1-101 m/z = 692.23(C₅₀H₃₂N₂S =692.87) P1-102 m/z = 692.23(C₅₀H₃₂N₂S = 692.87) P1-103 m/z =718.24(C₅₂H₃₄N₂S = 718.90) P1-104 m/z = 882.31(C₆₅H₄₂N₂S = 883.11)P1-105 m/z = 676.25(C₅₀H₃₂N₂O = 676.80) P1-106 m/z = 676.25(C₅₀H₃₂N₂O =676.80) P1-107 m/z = 702.27(C₅₂H₃₄N₂O = 702.84) P1-108 m/z =866.33(C₆₅H₄₂N₂O = 867.04) P1-109 m/z = 826.33(C₆₃H₄₂N₂ = 827.02) P1-110m/z = 826.33(C₆₃H₄₂N₂ = 827.02) P1-111 m/z = 742.24(C₅₄H₃₄N₂S = 742.93)P1-112 m/z = 726.27(C₅₄H₃₄N₂O = 726.86) P2-1 m/z = 486.21(C₃₆H₂₆N₂ =486.61) P2-2 m/z = 562.24(C₄₂H₃₀N₂ = 562.70) P2-3 m/z = 562.24(C₄₂H₃₀N₂= 562.70) P2-4 m/z = 638.27(C₄₈H₃₄N₂ = 638.80) P2-5 m/z =586.24(C₄₄H₃₀N₂ = 586.72) P2-6 m/z = 586.24(C₄₄H₃₀N₂ = 586.72) P2-7 m/z= 612.26(C₄₆H₃₂N₂ = 612.76) P2-8 m/z = 726.30(C₅₅H₃₈N₂ = 726.90) P2-9m/z = 638.27(C₄₈H₃₄N₂ = 638.80) P2-10 m/z = 800.32(C₆₁H₄₀N₂ = 800.98)P2-11 m/z = 536.23(C₄₀H₂₈N₂ = 536.66) P2-12 m/z = 688.29(C₅₂H₃₆N₂ =688.86) P2-13 m/z = 852.35(C₆₅H₄₄N₂ = 853.06) P2-14 m/z =638.27(C₄₈H₃₄N₂ = 638.80) P2-15 m/z = 688.29(C₅₂H₃₆N₂ = 688.86) P2-16m/z = 662.27(C₅₀H₃₄N₂ = 662.82) P2-17 m/z = 718.24(C₅₂H₃₄N₂S = 718.90)P2-18 m/z = 702.27(C₅₂H₃₄N₂O = 702.84) P2-19 m/z = 664.26(C₄₈H₃₂N₄ =664.79) P2-20 m/z = 664.26(C₄₈H₃₂N₄ = 664.79) P2-21 m/z =562.24(C₄₂H₃₀N₂ = 562.70) P2-22 m/z = 562.24(C₄₂H₃₀N₂ = 562.70) P2-23m/z = 780.35(C₅₆H₄₈N₂S = 781.06) P2-24 m/z = 665.26(C₄₇H₃₁N₅ = 665.78)P2-25 m/z = 526.24(C₃₉H₃₀N₂ = 526.67) P2-26 m/z = 739.30(C₅₅H₃₇N₃ =739.90) P2-27 m/z = 642.27(C₄₇H₃₄N₂O = 642.79) P2-28 m/z =790.31(C₅₈H₃₈N₄ = 790.95) P2-29 m/z = 726.30(C₅₅H₃₈N₂ = 726.90) P2-30m/z = 802.33(C₆₁H₄₂N₂ = 803.00) P2-31 m/z = 802.33(C₆₁H₄₂N₂ = 803.00)P2-32 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-33 m/z = 726.30(C₅₅H₃₈N₂ =726.90) P2-34 m/z = 726.30(C₅₅H₃₈N₂ = 726.90) P2-35 m/z =852.35(C₆₅H₄₄N₂ = 853.06) P2-36 m/z = 1016.41(C₇₈H₅₂N₂ = 1017.26) P2-37m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-38 m/z = 1040.41(C₈₀H₅₂N₂ = 1041.28)P2-39 m/z = 776.32(C₅₉H₄₀N₂ = 776.96) P2-40 m/z = 878.37(C₆₇H₄₆N₂ =879.10) P2-41 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-42 m/z =878.37(C₆₇H₄₆N₂ = 879.10) P2-43 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-44m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-45 m/z = 726.30(C₅₅H₃₈N₂ = 726.90)P2-46 m/z = 802.33(C₆₁H₄₂N₂ = 803.00) P2-47 m/z = 802.33(C₆₁H₄₂N₂ =803.00) P2-48 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-49 m/z =826.33(C₆₃H₄₂N₂ = 827.02) P2-50 m/z = 826.33(C₆₃H₄₂N₂ = 827.02) P2-51m/z = 852.35(C₆₅H₄₄N₂ = 853.06) P2-52 m/z = 1016.41(C₇₈H₅₂N₂ = 1017.26)P2-53 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-54 m/z = 1040.41(C₈₀H₅₂N₂ =1041.28) P2-55 m/z = 776.32(C₅₉H₄₀N₂ = 776.96) P2-56 m/z =878.37(C₆₇H₄₆N₂ = 879.10) P2-57 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-58m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-59 m/z = 878.37(C₆₇H₄₆N₂ = 879.10)P2-60 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-61 m/z = 726.30(C₅₅H₃₈N₂ =726.90) P2-62 m/z = 802.33(C₆₁H₄₂N₂ = 803.00) P2-63 m/z =802.33(C₆₁H₄₂N₂ = 803.00) P2-64 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-65m/z = 826.33(C₆₃H₄₂N₂ = 827.02) P2-66 m/z = 826.33(C₆₃H₄₂N₂ = 827.02)P2-67 m/z = 852.35(C₆₅H₄₄N₂ = 853.06) P2-68 m/z = 1016.41(C₇₈H₅₂N₂ =1017.26) P2-69 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-70 m/z =1040.41(C₈₀H₅₂N₂ = 1041.28) P2-71 m/z = 776.32(C₅₉H₄₀N₂ = 776.96) P2-72m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-73 m/z = 878.37(C₆₇H₄₆N₂ = 879.10)P2-74 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-75 m/z = 878.37(C₆₇H₄₆N₂ =879.10) P2-76 m/z = 878.37(C₆₇H₄₆N₂ = 879.10) P2-77 m/z =638.27(C₄₈H₃₄N₂ = 638.80) P2-78 m/z = 714.30(C₅₄H₃₈N₂ = 714.89) P2-79m/z = 714.30(C₅₄H₃₈N₂ = 714.89) P2-80 m/z = 790.33(C₆₀H₄₂N₂ = 790.99)P2-81 m/z = 738.30(C₅₆H₃₈N₂ = 738.91) P2-82 m/z = 738.30(C₅₆H₃₈N₂ =738.91) P2-83 m/z = 764.32(C₅₈H₄₀N₂ = 764.95) P2-84 m/z =928.38(C₇₁H₄₈N₂ = 929.15) P2-85 m/z = 790.33(C₆₀H₄₂N₂ = 790.99) P2-86m/z = 638.27(C₄₈H₃₄N₂ = 638.80) P2-87 m/z = 638.27(C₄₈H₃₄N₂ = 638.80))P2-88 m/z = 638.27(C₄₈H₃₄N₂ = 638.80) P2-89 m/z = 648.33(C₄₈H₂₄D₁₀N₂ =648.86) P2-90 m/z = 724.37(C₅₄H₂₈D₁₀N₂ = 724.95) P2-91 m/z =795.37(C₆₀H₃₇D₅N₂ = 796.02) P2-92 m/z = 643.30(C₄₈H₂₉D₅N₂ = 643.83)P2-93 m/z = 776.32(C₅₉H₄₀N₂ = 776.96) P2-94 m/z = 826.33(C₆₃H₄₂N₂ =827.02) P2-95 m/z = 776.32(C₅₉H₄₀N₂ = 776.96) P2-96 m/z =826.33(C₆₃H₄₂N₂ = 827.02) P2-97 m/z = 854.37(C₆₅H₄₆N₂ = 855.07) P2-98m/z = 836.34(C₆₁H₄₄N₂O₂ = 837.01) P2-99 m/z = 826.33(C₆₃H₄₂N₂ = 827.02)P2-100 m/z = 826.33(C₆₃H₄₂N₂ = 827.02) P2-101 m/z = 692.23(C₅₀H₃₂N₂S =692.87) P2-102 m/z = 692.23(C₅₀H₃₂N₂S = 692.87) P2-103 m/z =718.24(C₅₂H₃₄N₂S = 718.90) P2-104 m/z = 882.31(C₆₅H₄₂N₂S = 883.11)P2-105 m/z = 676.25(C₅₀H₃₂N₂O = 676.80) P2-106 m/z = 676.25(C₅₀H₃₂N₂O =676.80) P2-107 m/z = 702.27(C₅₂H₃₄N₂O = 702.84) P2-108 m/z =866.33(C₆₅H₄₂N₂O = 867.04) P2-109 m/z = 826.33(C₆₃H₄₂N₂ = 827.02) P2-110m/z = 826.33(C₆₃H₄₂N₂ = 827.02) P2-111 m/z = 742.24(C₅₄H₃₄N₂S = 742.93)P2-112 m/z = 726.27(C₅₄H₃₄N₂O = 726.86) P3-1 m/z = 562.24(C₄₂H₃₀N₂ =562.70) P3-2 m/z = 668.23(C₄₈H₃₂N₂S = 668.85) P3-3 m/z =728.28(C₅₄H₃₆N₂O = 728.88) P3-4 m/z = 754.33(C₅₇H₄₂N₂ = 754.96) P3-5 m/z= 802.33(C₆₁H₄₂N₂ = 803.00) P3-6 m/z = 800.32(C₆₁H₄₀N₂ = 800.98) P3-7m/z = 612.26(C₄₆H₃₂N₂ = 612.76) P3-8 m/z = 718.24(C₅₂H₃₄N₂S = 718.90)P3-9 m/z = 804.31(C₆₀H₄₀N₂O = 804.97) P3-10 m/z = 754.33(C₅₇H₄₂N₂ =754.96) P3-11 m/z = 928.38(C₇₁H₄₈N₂ = 929.15) P3-12 m/z =926.37(C₇₁H₄₆N₂ = 927.14) P3-13 m/z = 688.29(C₅₂H₃₆N₂ = 688.86) P3-14m/z = 794.28(C₅₈H₃₈N₂S = 795.00) P3-15 m/z = 729.28(C₅₃H₃₅N₃O = 729.86)P3-16 m/z = 805.35(C₆₀H₄₃N₃ = 806.00) P3-17 m/z = 854.34(C₆₃H₄₂N₄ =855.03) P3-18 m/z = 802.31(C₅₉H₃₈N₄ = 802.96) P3-19 m/z =562.24(C₄₂H₃₀N₂ = 562.70) P3-20 m/z = 668.23(C₄₈H₃₂N₂S = 668.85) P3-21m/z = 728.28(C₅₄H₃₆N₂O = 728.88) P3-22 m/z = 754.33(C₅₇H₄₂N₂ = 754.96)P3-23 m/z = 802.33(C₆₁H₄₂N₂ = 803.00) P3-24 m/z = 800.32(C₆₁H₄₀N₂ =800.98) P3-25 m/z = 612.26(C₄₆H₃₂N₂ = 612.76) P3-26 m/z =718.24(C₅₂H₃₄N₂S = 718.90) P3-27 m/z = 804.31(C₆₀H₄₀N₂O = 804.97) P3-28m/z = 754.33(C₅₇H₄₂N₂ = 754.96) P3-29 m/z = 928.38(C₇₁H₄₈N₂ = 929.15)P3-30 m/z = 926.37(C₇₁H₄₆N₂ = 927.14) P3-31 m/z = 688.29(C₅₂H₃₆N₂ =688.86) P3-32 m/z = 794.28(C₅₈H₃₈N₂S = 795.00) P3-33 m/z =729.28(C₅₃H₃₅N₃O = 729.86) P3-34 m/z = 805.35(C₆₀H₄₃N₃ = 806.00) P3-35m/z = 854.34(C₆₃H₄₂N₄ = 855.03) P3-36 m/z = 802.31(C₅₉H₃₈N₄ = 802.96)P3-37 m/z = 714.30(C₅₄H₃₈N₂ = 714.89) P3-38 m/z = 714.30(C₅₄H₃₈N₂ =714.89) P4-1 m/z = 816.33(C₆₀H₄₀N₄ = 816.99) P4-2 m/z = 727.30(C₅₄H₃₇N₃= 727.89) P4-3 m/z = 741.28(C₅₄H₃₅N₃O = 741.88) P4-4 m/z =757.26(C₅₄H₃₅N₃S = 757.94) P4-5 m/z = 701.28(C₅₂H₃₅N₃ = 701.85) P4-6 m/z= 803.33(C₆₀H₄₁N₃ = 803.99) P4-7 m/z = 757.26(C₅₄H₃₅N₃S = 757.94) P4-8m/z = 909.32(C₆₆H₄₃N₃S = 910.13) P4-9 m/z = 767.33(C₅₇H₄₁N₃ = 767.96)P4-10 m/z = 833.29(C₆₀H₃₉N₃S = 834.04) P4-11 m/z = 701.28(C₅₂H₃₅N₃ =701.85) P4-12 m/z = 807.27(C₅₈H₃₇N₃S = 808.00) P4-13 m/z =803.33(C₆₀H₄₁N₃ = 803.99) P4-14 m/z = 727.30(C₅₄H₃₇N₃ = 727.89) P4-15m/z = 833.29(C₆₀H₃₉N₃S = 834.04) P4-16 m/z = 777.31(C₅₈H₃₉N₃ = 777.95)P4-17 m/z = 727.30(C₅₄H₃₇N₃ = 727.89) P4-18 m/z = 777.31(C₅₈H₃₉N₃ =777.95) P4-19 m/z = 757.26(C₅₄H₃₅N₃S = 757.94) P4-20 m/z =767.33(C₅₇H₄₁N₃ = 767.96) P4-21 m/z = 817.35(C₆₁H₄₃N₃ = 818.01) P4-22m/z = 727.30(C₅₄H₃₇N₃ = 727.89) P4-23 m/z = 892.36(C₆₆H₄₄N₄ = 893.08)P4-24 m/z = 891.36(C₆₇H₄₅N₃ = 892.09) P4-25 m/z = 777.31(C₅₈H₃₉N₃ =777.95) P4-26 m/z = 817.35(C₆₁H₄₃N₃ = 818.01) P4-27 m/z =803.33(C₆₀H₄₁N₃ = 803.99) P4-28 m/z = 777.31(C₅₈H₃₉N₃ = 777.95) P4-29m/z = 777.31(C₅₈H₃₉N₃ = 777.95) P4-30 m/z = 777.31(C₅₈H₃₉N₃ = 777.95)P4-31 m/z = 778.31(C₅₇H₃₈N₄ = 778.94) P4-32 m/z = 943.39(C₇₁H₄₉N₃ =944.17) P4-33 m/z = 882.35(C₆₃H₄₂N₆ = 883.05) P4-34 m/z =732.33(C₅₄H₃₂D₅N₃ = 732.92) P4-35 m/z = 833.29(C₆₀H₃₉N₃S = 834.04) P4-36m/z = 732.33(C₅₄H₃₂D₅N₃ = 732.92)

Fabrication and Evaluation of Organic Electronic Element Example 1 GreenOLEDs (A Hole Transport Layer)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as ahole transport layer material.

First, an ITO layer (anode) was formed on a glass substrate, and a filmof 4,4′,4″-Tris[2-naphthyl(phenyl)amino]triphenylamine (“2-TNATA”) wasvacuum-deposited on the ITO layer to form a hole injection layer with athickness of 60 nm. Subsequently, P1-1 of the present invention wasvacuum-deposited with a thickness of 60 nm on the hole injection layerto form a hole transport layer.

Subsequently, a light emitting layer with a thickness of 30 nm wasdeposited on the hole transport layer by doping the hole transport layerwith 4,4′-N,N′-dicarbazole-biphenyl (“CBP”) as a host material andtris(2-phenylpyridine)-iridium (“Ir(ppy)₃)”) as a dopant material in aweight ratio of 90:10.

Next, a film of((1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (“BAlq”)was vacuum-deposited with a thickness of 10 nm on the light emittinglayer to form a hole blocking layer, and a film oftris(8-quinolinolato)aluminum (“Alq₃”) was formed with a thickness of 40nm to form an electron transport layer.

Next, LiF as halogenated alkali metal was deposited with a thickness of0.2 nm on the electron transport layer to form an electron injectionlayer, and then Al was deposited with a thickness of 150 nm on theelectron injection layer to form a cathode. In this way, the OLED wascompleted.

Example 2 to Example 256 Green OLEDs (A Hole Transport Layer)

The OLEDs were manufactured in the same manner as described in Example1, except that any one of the compounds P1-2 to P1-112, P2-1 to P2-112,P3-1 to P3-6, P3-19 to P3-24, P3-37 and P3-38 of the present inventionin the Table 4 below was used as the hole transport layer material,instead of the inventive compound P1-1.

Comparative Example 1

An OLED was manufactured in the same manner as described in Example 1,except that the following Comparative Compound 1 was used as the holetransport layer material, instead of the inventive compound P1-1.

Comparative Example 2

An OLED was manufactured in the same manner as described in Example 1,except that the following Comparative Compound 2 was used as the holetransport layer material, instead of the inventive compound P1-1.

Comparative Example 3

An OLED was manufactured in the same manner as described in Example 1,except that the following Comparative Compound 3 was used as the holetransport layer material, instead of the inventive compound P1-1.

Comparative Example 4

An OLED was manufactured in the same manner as described in Example 1,except that the following Comparative Compound 4 was used as the holetransport layer material, instead of the inventive compound P1-1.

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough the Examples 1 to 238 and the Comparative Examples 1 to 4, andelectro-luminescence (EL) characteristics of the OLED were measured byPR-650 (Photoresearch). Also, T90 life span was measured by life spanmeasuring equipment (Mcscience) at the reference brightness of 5000cd/m². Evaluation results are in the Table 4 below.

TABLE 4 Current Voltage Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) x y Com. Ex (1) Com. Com (1)5.6 17.9 5000.0 27.9 68.2 0.33 0.62 Com. Ex (2) Com. Com (2) 5.1 15.25000.0 33.0 115.9 0.33 0.61 Com. Ex (3) Com. Com (3) 5.3 13.0 5000.038.6 101.4 0.33 0.61 Com. Ex (4) Com. Com (4) 5.5 14.2 5000.0 35.1 100.90.33 0.61 Ex. (1) P1-1 5.3 10.2 5000.0 49.1 125.1 0.33 0.62 Ex. (2) P1-25.4 10.0 5000.0 49.8 138.4 0.33 0.61 Ex. (3) P1-3 5.5 10.8 5000.0 46.4121.2 0.33 0.61 Ex. (4) P1-4 5.4 11.0 5000.0 45.4 149.6 0.33 0.61 Ex.(5) P1-5 5.4 10.2 5000.0 49.2 143.2 0.33 0.62 Ex. (6) P1-6 5.3 10.45000.0 48.3 134.7 0.33 0.62 Ex. (7) P1-7 5.3 10.5 5000.0 47.6 114.8 0.330.61 Ex. (8) P1-8 5.5 10.9 5000.0 45.9 140.2 0.33 0.62 Ex. (9) P1-9 5.310.2 5000.0 49.0 104.7 0.33 0.61 Ex. (10) P1-10 5.5 10.4 5000.0 48.1107.3 0.33 0.62 Ex. (11) P1-11 5.4 10.1 5000.0 49.4 140.6 0.33 0.61 Ex.(12) P1-12 5.3 10.0 5000.0 49.9 136.9 0.33 0.61 Ex. (13) P1-13 5.4 10.55000.0 47.5 125.9 0.33 0.61 Ex. (14) P1-14 5.4 10.3 5000.0 48.5 129.60.33 0.62 Ex. (15) P1-15 5.4 10.3 5000.0 48.7 117.2 0.33 0.61 Ex. (16)P1-16 5.4 11.0 5000.0 45.5 134.9 0.33 0.61 Ex. (17) P1-17 5.5 10.85000.0 46.3 124.6 0.33 0.62 Ex. (18) P1-18 5.4 10.2 5000.0 48.9 117.80.33 0.61 Ex. (19) P1-19 5.5 11.0 5000.0 45.4 116.0 0.33 0.62 Ex. (20)P1-20 5.3 10.9 5000.0 45.9 118.4 0.33 0.62 Ex. (21) P1-21 5.5 10.75000.0 46.6 103.5 0.33 0.61 Ex. (22) P1-22 5.4 10.3 5000.0 48.7 126.50.33 0.62 Ex. (23) P1-23 5.5 11.0 5000.0 45.5 131.3 0.33 0.62 Ex. (24)P1-24 5.5 10.3 5000.0 48.4 139.0 0.33 0.62 Ex. (25) P1-25 5.5 10.85000.0 46.3 142.0 0.33 0.62 Ex. (26) P1-26 5.4 10.4 5000.0 48.2 112.50.33 0.61 Ex. (27) P1-27 5.4 10.1 5000.0 49.4 125.0 0.33 0.61 Ex. (28)P1-28 5.3 10.7 5000.0 46.7 109.0 0.33 0.61 Ex. (29) P1-29 5.5 10.95000.0 45.8 116.8 0.33 0.62 Ex. (30) P1-30 5.3 10.6 5000.0 47.1 108.80.33 0.62 Ex. (31) P1-31 5.5 11.0 5000.0 45.4 122.0 0.33 0.62 Ex. (32)P1-32 5.3 11.1 5000.0 45.1 104.5 0.33 0.61 Ex. (33) P1-33 5.4 10.15000.0 49.4 113.6 0.33 0.61 Ex. (34) P1-34 5.4 10.9 5000.0 45.8 104.90.33 0.62 Ex. (35) P1-35 5.4 10.7 5000.0 46.8 112.4 0.33 0.62 Ex. (36)P1-36 5.4 10.3 5000.0 48.6 140.7 0.33 0.61 Ex. (37) P1-37 5.3 10.15000.0 49.3 148.9 0.33 0.62 Ex. (38) P1-38 5.5 10.5 5000.0 47.6 141.10.33 0.61 Ex. (39) P1-39 5.5 10.1 5000.0 49.4 119.2 0.33 0.62 Ex. (40)P1-40 5.4 10.2 5000.0 49.1 140.0 0.33 0.61 Ex. (41) P1-41 5.4 10.65000.0 47.2 127.7 0.33 0.62 Ex. (42) P1-42 5.4 10.6 5000.0 47.3 126.20.33 0.61 Ex. (43) P1-43 5.3 11.1 5000.0 45.2 129.9 0.33 0.62 Ex. (44)P1-44 5.4 10.7 5000.0 46.6 146.3 0.33 0.62 Ex. (45) P1-45 5.3 11.05000.0 45.6 116.5 0.33 0.62 Ex. (46) P1-46 5.4 10.2 5000.0 49.1 133.90.33 0.61 Ex. (47) P1-47 5.5 10.8 5000.0 46.2 124.9 0.33 0.62 Ex. (48)P1-48 5.5 10.2 5000.0 48.8 144.4 0.33 0.61 Ex. (49) P1-49 5.4 10.35000.0 48.3 148.9 0.33 0.61 Ex. (50) P1-50 5.5 10.3 5000.0 48.4 139.40.33 0.61 Ex. (51) P1-51 5.4 10.3 5000.0 48.4 112.3 0.33 0.61 Ex. (52)P1-52 5.3 10.5 5000.0 47.6 116.9 0.33 0.62 Ex. (53) P1-53 5.5 10.25000.0 49.1 132.5 0.33 0.61 Ex. (54) P1-54 5.4 11.0 5000.0 45.6 115.20.33 0.62 Ex. (55) P1-55 5.5 10.5 5000.0 47.8 130.9 0.33 0.61 Ex. (56)P1-56 5.5 10.6 5000.0 47.0 101.8 0.33 0.61 Ex. (57) P1-57 5.3 10.35000.0 48.4 129.2 0.33 0.62 Ex. (58) P1-58 5.3 11.0 5000.0 45.6 138.70.33 0.61 Ex. (59) P1-59 5.5 10.5 5000.0 47.4 103.0 0.33 0.61 Ex. (60)P1-60 5.5 10.6 5000.0 47.2 144.0 0.33 0.61 Ex. (61) P1-61 5.3 10.85000.0 46.5 144.6 0.33 0.62 Ex. (62) P1-62 5.4 10.7 5000.0 46.9 136.50.33 0.61 Ex. (63) P1-63 5.3 10.9 5000.0 45.8 136.9 0.33 0.62 Ex. (64)P1-64 5.4 10.9 5000.0 45.9 148.7 0.33 0.62 Ex. (65) P1-65 5.5 10.55000.0 47.6 102.2 0.33 0.61 Ex. (66) P1-66 5.4 10.0 5000.0 49.8 116.50.33 0.62 Ex. (67) P1-67 5.4 10.6 5000.0 47.1 108.9 0.33 0.61 Ex. (68)P1-68 5.4 10.4 5000.0 47.9 129.8 0.33 0.62 Ex. (69) P1-69 5.4 11.15000.0 45.1 138.5 0.33 0.62 Ex. (70) P1-70 5.4 10.6 5000.0 47.0 144.40.33 0.62 Ex. (71) P1-71 5.3 10.4 5000.0 48.2 137.4 0.33 0.61 Ex. (72)P1-72 5.3 10.9 5000.0 45.7 127.3 0.33 0.62 Ex. (73) P1-73 5.3 10.35000.0 48.7 112.1 0.33 0.61 Ex. (74) P1-74 5.3 11.1 5000.0 45.0 140.80.33 0.61 Ex. (75) P1-75 5.3 10.1 5000.0 49.5 119.1 0.33 0.61 Ex. (76)P1-76 5.3 10.2 5000.0 49.2 127.2 0.33 0.62 Ex. (77) P1-77 5.5 10.15000.0 49.4 115.6 0.33 0.62 Ex. (78) P1-78 5.4 10.2 5000.0 48.8 121.90.33 0.61 Ex. (79) P1-79 5.4 10.3 5000.0 48.5 128.4 0.33 0.62 Ex. (80)P1-80 5.3 10.8 5000.0 46.3 142.9 0.33 0.61 Ex. (81) P1-81 5.4 10.15000.0 49.7 126.1 0.33 0.61 Ex. (82) P1-82 5.4 10.7 5000.0 46.5 130.20.33 0.62 Ex. (83) P1-83 5.5 10.2 5000.0 48.9 128.7 0.33 0.61 Ex. (84)P1-84 5.4 10.3 5000.0 48.7 114.1 0.33 0.61 Ex. (85) P1-85 5.4 10.55000.0 47.8 119.6 0.33 0.61 Ex. (86) P1-86 5.3 10.9 5000.0 45.8 142.80.33 0.62 Ex. (87) P1-87 5.4 10.6 5000.0 47.0 114.0 0.33 0.61 Ex. (88)P1-88 5.5 10.6 5000.0 47.3 120.6 0.33 0.62 Ex. (89) P1-89 5.5 11.05000.0 45.4 121.9 0.33 0.62 Ex. (90) P1-90 5.4 10.9 5000.0 45.8 108.00.33 0.61 Ex. (91) P1-91 5.3 10.8 5000.0 46.1 139.9 0.33 0.62 Ex. (92)P1-92 5.4 10.3 5000.0 48.7 111.4 0.33 0.61 Ex. (93) P1-93 5.5 10.05000.0 50.0 122.0 0.33 0.62 Ex. (94) P1-94 5.3 10.7 5000.0 46.8 109.50.33 0.61 Ex. (95) P1-95 5.5 10.3 5000.0 48.6 144.9 0.33 0.61 Ex. (96)P1-96 5.4 11.1 5000.0 45.1 137.9 0.33 0.62 Ex. (97) P1-97 5.4 10.15000.0 49.6 143.9 0.33 0.61 Ex. (98) P1-98 5.5 10.6 5000.0 47.1 130.90.33 0.62 Ex. (99) P1-99 5.3 10.7 5000.0 46.5 147.2 0.33 0.62 Ex. (100)P1-100 5.3 10.8 5000.0 46.3 108.6 0.33 0.61 Ex. (101) P1-101 5.3 10.15000.0 49.3 124.4 0.33 0.61 Ex. (102) P1-102 5.3 10.3 5000.0 48.5 132.00.33 0.61 Ex. (103) P1-103 5.3 11.0 5000.0 45.6 142.0 0.33 0.62 Ex.(104) P1-104 5.4 10.6 5000.0 47.3 131.6 0.33 0.62 Ex. (105) P1-105 5.310.9 5000.0 46.0 126.8 0.33 0.62 Ex. (106) P1-106 5.4 10.5 5000.0 47.7131.9 0.33 0.61 Ex. (107) P1-107 5.4 10.2 5000.0 49.0 138.4 0.33 0.61Ex. (108) P1-108 5.5 10.6 5000.0 47.2 130.5 0.33 0.62 Ex. (109) P1-1095.4 11.0 5000.0 45.4 104.3 0.33 0.62 Ex. (110) P1-110 5.5 10.4 5000.048.3 105.0 0.33 0.62 Ex. (111) P1-111 5.5 10.2 5000.0 48.9 127.1 0.330.61 Ex. (112) P1-112 5.4 10.5 5000.0 47.8 121.9 0.33 0.61 Ex. (113)P2-1 5.4 12.0 5000.0 41.7 128.7 0.33 0.61 Ex. (114) P2-2 5.4 11.2 5000.044.6 139.5 0.33 0.61 Ex. (115) P2-3 5.3 12.3 5000.0 40.6 137.4 0.33 0.61Ex. (116) P2-4 5.4 11.6 5000.0 43.2 143.3 0.33 0.62 Ex. (117) P2-5 5.411.8 5000.0 42.3 126.1 0.33 0.61 Ex. (118) P2-6 5.4 11.4 5000.0 44.0117.9 0.33 0.62 Ex. (119) P2-7 5.4 11.3 5000.0 44.1 137.9 0.33 0.61 Ex.(120) P2-8 5.5 11.1 5000.0 45.0 113.7 0.33 0.62 Ex. (121) P2-9 5.4 11.75000.0 42.6 136.6 0.33 0.61 Ex. (122) P2-10 5.4 11.3 5000.0 44.4 111.70.33 0.62 Ex. (123) P2-11 5.3 11.8 5000.0 42.3 147.2 0.33 0.61 Ex. (124)P2-12 5.4 11.3 5000.0 44.2 100.4 0.33 0.61 Ex. (125) P2-13 5.4 12.35000.0 40.6 128.7 0.33 0.61 Ex. (126) P2-14 5.5 11.6 5000.0 43.0 125.40.33 0.62 Ex. (127) P2-15 5.4 11.6 5000.0 43.2 132.3 0.33 0.61 Ex. (128)P2-16 5.5 11.6 5000.0 43.0 120.3 0.33 0.62 Ex. (129) P2-17 5.3 12.25000.0 41.1 141.2 0.33 0.62 Ex. (130) P2-18 5.4 12.3 5000.0 40.6 129.30.33 0.62 Ex. (131) P2-19 5.4 12.2 5000.0 41.0 126.2 0.33 0.61 Ex. (132)P2-20 5.3 11.7 5000.0 42.6 132.3 0.33 0.62 Ex. (133) P2-21 5.4 12.05000.0 41.8 127.9 0.33 0.62 Ex. (134) P2-22 5.5 11.3 5000.0 44.2 141.80.33 0.61 Ex. (135) P2-23 5.4 11.6 5000.0 43.0 116.7 0.33 0.62 Ex. (136)P2-24 5.4 12.5 5000.0 40.1 113.0 0.33 0.61 Ex. (137) P2-25 5.3 12.35000.0 40.5 107.7 0.33 0.61 Ex. (138) P2-26 5.5 12.4 5000.0 40.4 107.70.33 0.61 Ex. (139) P2-27 5.3 12.5 5000.0 40.1 147.2 0.33 0.61 Ex. (140)P2-28 5.4 11.4 5000.0 43.7 143.1 0.33 0.61 Ex. (141) P2-29 5.4 11.55000.0 43.6 104.9 0.33 0.62 Ex. (142) P2-30 5.4 11.9 5000.0 41.9 129.50.33 0.62 Ex. (143) P2-31 5.5 12.2 5000.0 41.1 129.9 0.33 0.62 Ex. (144)P2-32 5.5 12.3 5000.0 40.8 137.8 0.33 0.61 Ex. (145) P2-33 5.4 11.25000.0 44.6 126.9 0.33 0.61 Ex. (146) P2-34 5.4 12.5 5000.0 40.1 108.10.33 0.62 Ex. (147) P2-35 5.4 11.9 5000.0 42.1 135.4 0.33 0.62 Ex. (148)P2-36 5.3 12.2 5000.0 40.9 106.3 0.33 0.62 Ex. (149) P2-37 5.5 11.95000.0 42.1 102.7 0.33 0.62 Ex. (150) P2-38 5.3 11.3 5000.0 44.3 137.20.33 0.62 Ex. (151) P2-39 5.4 12.2 5000.0 41.0 132.0 0.33 0.61 Ex. (152)P2-40 5.4 11.7 5000.0 42.6 135.3 0.33 0.61 Ex. (153) P2-41 5.4 11.75000.0 42.9 130.5 0.33 0.62 Ex. (154) P2-42 5.5 11.4 5000.0 43.9 126.10.33 0.62 Ex. (155) P2-43 5.3 11.9 5000.0 42.0 111.7 0.33 0.62 Ex. (156)P2-44 5.4 11.5 5000.0 43.4 121.9 0.33 0.61 Ex. (157) P2-45 5.4 11.75000.0 42.9 142.8 0.33 0.61 Ex. (158) P2-46 5.4 12.4 5000.0 40.2 121.00.33 0.61 Ex. (159) P2-47 5.5 12.1 5000.0 41.4 134.9 0.33 0.61 Ex. (160)P2-48 5.5 12.0 5000.0 41.8 107.9 0.33 0.62 Ex. (161) P2-49 5.4 11.55000.0 43.3 109.4 0.33 0.62 Ex. (162) P2-50 5.4 11.4 5000.0 43.8 116.00.33 0.62 Ex. (163) P2-51 5.4 12.4 5000.0 40.2 128.9 0.33 0.62 Ex. (164)P2-52 5.4 11.8 5000.0 42.4 139.9 0.33 0.62 Ex. (165) P2-53 5.5 11.25000.0 44.5 148.4 0.33 0.62 Ex. (166) P2-54 5.5 12.4 5000.0 40.4 108.10.33 0.62 Ex. (167) P2-55 5.5 11.2 5000.0 44.6 145.4 0.33 0.62 Ex. (168)P2-56 5.4 11.4 5000.0 44.0 108.7 0.33 0.61 Ex. (169) P2-57 5.4 12.15000.0 41.2 135.0 0.33 0.61 Ex. (170) P2-58 5.5 12.3 5000.0 40.6 110.60.33 0.62 Ex. (171) P2-59 5.4 11.4 5000.0 43.9 147.2 0.33 0.61 Ex. (172)P2-60 5.4 12.5 5000.0 40.1 113.1 0.33 0.62 Ex. (173) P2-61 5.4 11.35000.0 44.2 143.9 0.33 0.62 Ex. (174) P2-62 5.4 11.7 5000.0 42.6 138.20.33 0.61 Ex. (175) P2-63 5.5 11.4 5000.0 43.9 138.4 0.33 0.62 Ex. (176)P2-64 5.5 11.7 5000.0 42.8 102.3 0.33 0.61 Ex. (177) P2-65 5.4 12.35000.0 40.7 143.3 0.33 0.61 Ex. (178) P2-66 5.4 11.5 5000.0 43.5 105.80.33 0.62 Ex. (179) P2-67 5.4 11.7 5000.0 42.7 142.8 0.33 0.62 Ex. (180)P2-68 5.4 11.4 5000.0 43.9 141.9 0.33 0.61 Ex. (181) P2-69 5.4 11.25000.0 44.7 146.5 0.33 0.62 Ex. (182) P2-70 5.5 11.3 5000.0 44.2 147.30.33 0.62 Ex. (183) P2-71 5.4 11.6 5000.0 43.1 142.0 0.33 0.61 Ex. (184)P2-72 5.4 11.6 5000.0 43.2 136.0 0.33 0.62 Ex. (185) P2-73 5.4 12.15000.0 41.2 137.8 0.33 0.61 Ex. (186) P2-74 5.4 11.5 5000.0 43.3 111.10.33 0.62 Ex. (187) P2-75 5.3 11.8 5000.0 42.4 129.3 0.33 0.62 Ex. (188)P2-76 5.4 11.4 5000.0 43.9 100.8 0.33 0.61 Ex. (189) P2-77 5.4 11.45000.0 43.8 131.5 0.33 0.61 Ex. (190) P2-78 5.3 11.2 5000.0 44.8 114.30.33 0.62 Ex. (191) P2-79 5.4 11.4 5000.0 44.0 116.1 0.33 0.61 Ex. (192)P2-80 5.5 11.6 5000.0 43.2 116.1 0.33 0.61 Ex. (193) P2-81 5.4 11.25000.0 44.7 123.3 0.33 0.62 Ex. (194) P2-82 5.4 11.4 5000.0 43.8 148.30.33 0.61 Ex. (195) P2-83 5.5 11.3 5000.0 44.1 135.3 0.33 0.61 Ex. (196)P2-84 5.5 12.2 5000.0 40.9 128.0 0.33 0.61 Ex. (197) P2-85 5.5 11.65000.0 43.0 139.1 0.33 0.61 Ex. (198) P2-86 5.4 11.7 5000.0 42.7 125.30.33 0.62 Ex. (199) P2-87 5.3 11.1 5000.0 45.0 140.8 0.33 0.62 Ex. (200)P2-88 5.5 11.6 5000.0 43.0 101.5 0.33 0.61 Ex. (201) P2-89 5.4 11.15000.0 45.0 133.6 0.33 0.61 Ex. (202) P2-90 5.5 11.2 5000.0 44.6 141.80.33 0.62 Ex. (203) P2-91 5.3 11.9 5000.0 42.0 149.2 0.33 0.62 Ex. (204)P2-92 5.3 11.5 5000.0 43.4 120.3 0.33 0.62 Ex. (205) P2-93 5.4 11.65000.0 43.2 121.9 0.33 0.62 Ex. (206) P2-94 5.5 11.3 5000.0 44.4 145.60.33 0.61 Ex. (207) P2-95 5.5 11.8 5000.0 42.2 122.0 0.33 0.61 Ex. (208)P2-96 5.4 11.5 5000.0 43.5 134.2 0.33 0.61 Ex. (209) P2-97 5.3 11.75000.0 42.9 114.2 0.33 0.62 Ex. (210) P2-98 5.4 11.7 5000.0 42.7 142.40.33 0.62 Ex. (211) P2-99 5.5 12.2 5000.0 40.9 112.8 0.33 0.62 Ex. (212)P2-100 5.4 11.7 5000.0 42.6 142.0 0.33 0.61 Ex. (213) P2-101 5.3 11.65000.0 43.1 127.1 0.33 0.61 Ex. (214) P2-102 5.5 11.7 5000.0 42.9 143.40.33 0.61 Ex. (215) P2-103 5.5 12.2 5000.0 40.8 106.6 0.33 0.62 Ex.(216) P2-104 5.5 11.9 5000.0 42.0 100.8 0.33 0.61 Ex. (217) P2-105 5.411.7 5000.0 42.6 108.6 0.33 0.62 Ex. (218) P2-106 5.4 12.4 5000.0 40.2138.3 0.33 0.62 Ex. (219) P2-107 5.5 12.1 5000.0 41.3 130.2 0.33 0.61Ex. (220) P2-108 5.5 11.6 5000.0 43.0 111.0 0.33 0.62 Ex. (221) P2-1095.5 12.2 5000.0 41.0 126.4 0.33 0.62 Ex. (222) P2-110 5.4 11.6 5000.043.1 120.7 0.33 0.61 Ex. (223) P2-111 5.4 12.2 5000.0 41.0 107.3 0.330.61 Ex. (224) P2-112 5.5 12.4 5000.0 40.2 138.3 0.33 0.61 Ex. (225)P3-1 5.5 11.5 5000.0 43.3 128.1 0.33 0.62 Ex. (226) P3-2 5.5 12.1 5000.041.3 143.0 0.33 0.62 Ex. (227) P3-3 5.3 11.4 5000.0 43.9 96.3 0.33 0.61Ex. (228) P3-4 5.4 12.2 5000.0 41.0 105.8 0.33 0.62 Ex. (229) P3-5 5.412.0 5000.0 41.7 145.1 0.33 0.62 Ex. (230) P3-6 5.5 11.6 5000.0 42.9124.4 0.33 0.61 Ex. (231) P3-19 5.5 10.1 5000.0 49.4 148.0 0.33 0.61 Ex.(232) P3-20 5.3 10.4 5000.0 48.1 94.6 0.33 0.61 Ex. (233) P3-21 5.4 10.45000.0 48.1 107.8 0.33 0.62 Ex. (234) P3-22 5.4 10.6 5000.0 47.3 104.90.33 0.62 Ex. (235) P3-23 5.4 10.9 5000.0 45.7 112.1 0.33 0.61 Ex. (236)P3-24 5.5 10.2 5000.0 48.9 144.6 0.33 0.62 Ex. (237) P3-37 5.5 10.45000.0 48.1 99.5 0.33 0.62 Ex. (238) P3-38 5.4 11.4 5000.0 44.0 110.60.33 0.61

It can be seen from the results in Table 4 above, that the OLEDsemploying the inventive compounds as a hole transport layer materialsshowed predominantly improved efficiency and lifespan, compared to theOLEDs employing comparative compounds 1 to 4 as a hole transport layermaterials. Especially, it can be seen that the OLEDs employing theinventive compounds showed predominantly improved efficiency andlifespan, compared to the Comparative Example 1 employing comparativecompound 1 of which structure is different from the inventive compound.

Further, referring to the Comparative Example 2 to 4 employingcomparative compounds 2 to 4 that have carbazole as core as thestructure in the present invention, the OLED employing comparativecompound 2 where a linker is linked to 2-position of the carbazolemoiety (‘Com. Ex(3) and ‘Com. Ex(4)’) showed higher drive voltage andshorter life span yet higher efficiency, compared to the OLED employingcomparative compounds where a linker is linked to 3-position of thecarbazole moiety (‘Com. Ex(2)). Comparing OLEDs employing the inventivecompounds having a non-linear phenyl linker and the OLED of Com. Ex(4)having a non-linear biphenyl linker, the efficiency of OLEDs employingthe inventive compounds is higher than the OLED of Com. Ex(4).

From the result in Table 4, it is seen that the OLEDs employing as ahole transport layer material, the compound of the present inventionwherein the linker phenyl is linked to 2-position of carbazolederivative and an amine group is linked on ortho- or meta-position ofthe phenyl, showed high efficiency, compared to the OLED of Com. Ex (4)wherein the linker biphenyl is linked to 2-position of carbazolederivative and the amine group is linked to biphenyl on meta position.

These results are believed to come from that in a compound where thelinker is linked on 2-position of the carbazole core, the conjugationlength gets shorter than in a compound where the linker is linked on3-position of the carbazole core, and the band gap gets widened and theHOMO value gets deepen.

Further, it is seen that where an amine group is linked on ortho- ormeta-position of a linker and the linker is not biphenyl but phenyl asthe inventive invention, the bonding angle gets decreased than in a casewhere the amine group is linked linear to the linker on para-position,and the T1 values get higher, and as a result the electron blockingabilities are improved.

Therefore, the OLED employing the inventive compound as a hole transportlayer material has deep HOMO values and the improved electron blockingabilities, and as a result the exciton is more easily produced toimprove efficiency and lengthen lifespan.

Considering the characteristics(deep HOMO energy level, high T1 value,heat-stability) described above together, it can be seen that the bandgap and electrical properties, as well as the surface properties canchange much depending on the linking position of the carbazole core andthe amine, and which the linker is phenyl or biphenyl, which can be mainfactors in improving performance of the organic electric elements.

Furthermore, properties from the hole transport layer should beconsidered in relation with the light emitting layer(host), and oneskilled in the art, even using a similar core compound, would havedifficulty in inferring the characteristics shown by the hole transportlayer using the compound of the present invention.

Example 239 An Emission-Auxiliary Layer (Red)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as anemission-auxiliary layer material.

First, an ITO layer (anode) was formed on a glass substrate, and a filmof 2-TNATA was vacuum-deposited on the ITO layer to form a holeinjection layer with a thickness of 60 nm. Subsequently,N,N′-Bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine(“NPD”) was vacuum-deposited with a thickness of 60 nm on the holeinjection layer to form a hole transport layer.

Subsequently, a film of the compound P1-1 of the present invention wasvacuum-deposited on the hole transport layer to form aemission-auxiliary layer with a thickness of 20 nm.

A light emitting layer with a thickness of 30 nm was deposited on theemission-auxiliary layer by using the CBP as a host material andbis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (“(piq)₂-Ir(acac)”)as a dopant material in a weight ratio of 95:5.

Next, a film of BAlq was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, and a film ofAlq₃ was formed with a thickness of 40 nm to form an electron transportlayer.

Next, LiF as halogenated alkali metal was deposited with a thickness of0.2 nm on the electron transport layer to form an electron injectionlayer, and then Al was deposited with a thickness of 150 nm on theelectron injection layer to form a cathode. In this way, the OLED wascompleted.

Example 240 to Example 365 An Emission-Auxiliary Layer (Red)

The OLED was manufactured in the same manner as described in TestExample 239, except that any one of the compounds P1-2 to P1-20, P1-45to P1-52, P1-61 to P1-64, P1-101 to P1-108, P2-1 to P2-20, P2-45 toP2-52, P2-61 to P2-64, P2-101 to P2-108, P3-1 to P3-38, P4-2, P4-5, P4-8to P4-10, P4-17, P4-20, P4-22 and P4-24 of the present invention in theTable 5 below was used as the emission-auxiliary layer material, insteadof the inventive compound P1-1.

Comparative Example 5

An OLED was manufactured in the same manner as described in Test Example239, except that Comparative Compound 2 above was used as theemission-auxiliary layer material, instead of the inventive compoundP1-1.

Comparative Example 6

An OLED was manufactured in the same manner as described in Test Example239, except that Comparative Compound 3 above was used as theemission-auxiliary layer material, instead of the inventive compoundP1-1.

Comparative Example 7

An OLED was manufactured in the same manner as described in Test Example239, except that Comparative Compound 4 above was used as theemission-auxiliary layer material, instead of the inventive compoundP1-1.

Comparative Example 8

An OLED was manufactured in the same manner as described in Test Example239, except not to form the emission-auxiliary layer.

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough Test Examples 239 to 365 and Comparative Examples 5 to 8, andelectro-luminescence (EL) characteristics of the OLED were measured byPR-650 (Photoresearch). Also, T95 life span was measured by life spanmeasuring equipment (Mcscience) at a reference brightness of 2500 cd/m².Table 5 below shows evaluation results of OLEDs manufactured TestExamples and Comparative Examples.

TABLE 5 Current Voltage Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) x y Com. Ex (5) Com. Com (2)5.9 26.5 2500.0 9.5 95.4 0.65 0.31 Com. Ex (6) Com. Com (3) 6.0 27.72500.0 9.0 96.1 0.64 0.34 Com. Ex (7) Com. Com (4) 6.1 26.4 2500.0 9.591.4 0.66 0.33 Com. Ex (8) — 5.7 33.3 2500.0 7.5 71.3 0.64 0.31 Ex.(239) P1-1 5.7 23.5 2500.0 10.7 117.6 0.64 0.32 Ex. (240) P1-2 5.6 22.72500.0 11.0 116.9 0.65 0.31 Ex. (241) P1-3 5.6 19.5 2500.0 12.8 117.10.66 0.32 Ex. (242) P1-4 5.6 19.4 2500.0 12.9 115.1 0.66 0.30 Ex. (243)P1-5 5.7 24.7 2500.0 10.1 116.9 0.66 0.32 Ex. (244) P1-6 5.6 19.7 2500.012.7 119.8 0.64 0.30 Ex. (245) P1-7 5.6 21.1 2500.0 11.8 116.2 0.66 0.33Ex. (246) P1-8 5.6 19.8 2500.0 12.6 115.1 0.65 0.30 Ex. (247) P1-9 5.724.7 2500.0 10.1 110.0 0.65 0.31 Ex. (248) P1-10 5.7 24.4 2500.0 10.2117.0 0.66 0.33 Ex. (249) P1-11 5.7 20.7 2500.0 12.1 115.9 0.65 0.32 Ex.(250) P1-12 5.6 21.9 2500.0 11.4 116.2 0.65 0.30 Ex. (251) P1-13 5.624.0 2500.0 10.4 114.4 0.65 0.34 Ex. (252) P1-14 5.7 23.7 2500.0 10.6112.4 0.64 0.34 Ex. (253) P1-15 5.7 19.4 2500.0 12.9 111.6 0.64 0.31 Ex.(254) P1-16 5.7 22.1 2500.0 11.3 114.8 0.65 0.32 Ex. (255) P1-17 5.622.1 2500.0 11.3 111.2 0.65 0.30 Ex. (256) P1-18 5.7 20.6 2500.0 12.2112.2 0.66 0.32 Ex. (257) P1-19 5.6 22.0 2500.0 11.3 112.4 0.64 0.31 Ex.(258) P1-20 5.6 22.3 2500.0 11.2 112.0 0.66 0.31 Ex. (259) P1-45 5.721.6 2500.0 11.6 111.0 0.65 0.30 Ex. (260) P1-46 5.6 20.0 2500.0 12.5113.9 0.64 0.31 Ex. (261) P1-47 5.6 20.9 2500.0 12.0 110.8 0.64 0.31 Ex.(262) P1-48 5.6 19.3 2500.0 13.0 117.2 0.65 0.33 Ex. (263) P1-49 5.625.0 2500.0 10.0 110.2 0.65 0.34 Ex. (264) P1-50 5.7 20.7 2500.0 12.1118.1 0.64 0.31 Ex. (265) P1-51 5.6 19.8 2500.0 12.6 113.1 0.65 0.31 Ex.(266) P1-52 5.7 22.4 2500.0 11.1 116.0 0.65 0.31 Ex. (267) P1-61 5.724.2 2500.0 10.3 116.4 0.65 0.33 Ex. (268) P1-62 5.6 23.8 2500.0 10.5116.2 0.66 0.31 Ex. (269) P1-63 5.6 23.1 2500.0 10.8 115.0 0.64 0.33 Ex.(270) P1-64 5.7 20.5 2500.0 12.2 111.3 0.64 0.31 Ex. (271) P1-101 5.620.9 2500.0 12.0 119.3 0.64 0.31 Ex. (272) P1-102 5.7 19.7 2500.0 12.7113.9 0.65 0.30 Ex. (273) P1-103 5.7 23.8 2500.0 10.5 116.8 0.65 0.34Ex. (274) P1-104 5.7 19.5 2500.0 12.8 116.2 0.66 0.33 Ex. (275) P1-1055.6 20.3 2500.0 12.3 116.7 0.66 0.31 Ex. (276) P1-106 5.7 22.9 2500.010.9 119.3 0.65 0.31 Ex. (277) P1-107 5.7 21.1 2500.0 11.9 115.2 0.660.32 Ex. (278) P1-108 5.6 23.9 2500.0 10.5 116.1 0.65 0.33 Ex. (279)P2-1 5.7 24.4 2500.0 10.3 118.8 0.65 0.33 Ex. (280) P2-2 5.6 22.4 2500.011.1 117.7 0.65 0.32 Ex. (281) P2-3 5.6 20.6 2500.0 12.1 119.9 0.65 0.31Ex. (282) P2-4 5.7 20.5 2500.0 12.2 111.9 0.64 0.30 Ex. (283) P2-5 5.722.2 2500.0 11.3 115.8 0.65 0.33 Ex. (284) P2-6 5.6 19.7 2500.0 12.7113.5 0.66 0.31 Ex. (285) P2-7 5.6 19.3 2500.0 12.9 112.6 0.64 0.31 Ex.(286) P2-8 5.6 21.0 2500.0 11.9 111.7 0.66 0.30 Ex. (287) P2-9 5.7 23.22500.0 10.8 118.4 0.65 0.31 Ex. (288) P2-10 5.6 20.9 2500.0 12.0 117.30.66 0.30 Ex. (289) P2-11 5.7 24.9 2500.0 10.0 111.8 0.65 0.33 Ex. (290)P2-12 5.6 19.4 2500.0 12.9 116.1 0.66 0.34 Ex. (291) P2-13 5.6 20.62500.0 12.1 119.4 0.66 0.31 Ex. (292) P2-14 5.6 20.6 2500.0 12.1 114.00.65 0.34 Ex. (293) P2-15 5.6 20.6 2500.0 12.1 116.0 0.65 0.32 Ex. (294)P2-16 5.6 23.2 2500.0 10.8 114.7 0.65 0.32 Ex. (295) P2-17 5.6 22.62500.0 11.0 114.2 0.64 0.30 Ex. (296) P2-18 5.6 24.5 2500.0 10.2 114.10.66 0.32 Ex. (297) P2-19 5.7 21.5 2500.0 11.6 113.9 0.66 0.30 Ex. (298)P2-20 5.6 20.1 2500.0 12.5 112.6 0.64 0.31 Ex. (299) P2-45 5.7 23.52500.0 10.6 116.1 0.66 0.30 Ex. (300) P2-46 5.6 23.3 2500.0 10.7 115.00.64 0.33 Ex. (301) P2-47 5.6 21.1 2500.0 11.9 112.1 0.66 0.33 Ex. (302)P2-48 5.6 21.8 2500.0 11.5 118.8 0.65 0.32 Ex. (303) P2-49 5.6 20.22500.0 12.4 114.8 0.65 0.32 Ex. (304) P2-50 5.7 22.9 2500.0 10.9 119.30.64 0.31 Ex. (305) P2-51 5.7 19.8 2500.0 12.6 119.3 0.65 0.33 Ex. (306)P2-52 5.7 21.5 2500.0 11.6 115.3 0.65 0.33 Ex. (307) P2-61 5.7 19.92500.0 12.6 115.2 0.66 0.32 Ex. (308) P2-62 5.7 22.0 2500.0 11.3 111.60.66 0.31 Ex. (309) P2-63 5.6 20.0 2500.0 12.5 111.5 0.65 0.31 Ex. (310)P2-64 5.7 24.9 2500.0 10.0 113.3 0.64 0.32 Ex. (311) P2-101 5.7 23.72500.0 10.5 115.6 0.65 0.31 Ex. (312) P2-102 5.7 23.6 2500.0 10.6 118.90.65 0.32 Ex. (313) P2-103 5.7 20.4 2500.0 12.3 113.0 0.65 0.31 Ex.(314) P2-104 5.7 22.3 2500.0 11.2 116.4 0.66 0.33 Ex. (315) P2-105 5.723.7 2500.0 10.6 110.5 0.66 0.34 Ex. (316) P2-106 5.7 24.3 2500.0 10.3115.3 0.66 0.31 Ex. (317) P2-107 5.7 21.6 2500.0 11.6 110.9 0.65 0.33Ex. (318) P2-108 5.6 21.6 2500.0 11.6 111.9 0.66 0.34 Ex. (319) P3-1 5.517.5 2500.0 14.3 128.9 0.65 0.32 Ex. (320) P3-2 5.6 17.6 2500.0 14.2129.4 0.65 0.32 Ex. (321) P3-3 5.6 16.8 2500.0 14.9 127.3 0.66 0.32 Ex.(322) P3-4 5.6 17.5 2500.0 14.3 123.5 0.66 0.31 Ex. (323) P3-5 5.5 17.12500.0 14.7 127.8 0.66 0.32 Ex. (324) P3-6 5.5 17.3 2500.0 14.4 123.90.65 0.34 Ex. (325) P3-7 5.5 17.6 2500.0 14.2 128.1 0.66 0.33 Ex. (326)P3-8 5.6 17.4 2500.0 14.3 126.5 0.65 0.30 Ex. (327) P3-9 5.6 17.4 2500.014.4 123.9 0.65 0.32 Ex. (328) P3-10 5.6 16.8 2500.0 14.9 126.3 0.650.30 Ex. (329) P3-11 5.5 17.6 2500.0 14.2 129.8 0.64 0.32 Ex. (330)P3-12 5.6 17.4 2500.0 14.3 123.4 0.65 0.32 Ex. (331) P3-13 5.5 17.12500.0 14.7 127.5 0.65 0.34 Ex. (332) P3-14 5.6 17.5 2500.0 14.3 125.80.66 0.34 Ex. (333) P3-15 5.6 17.4 2500.0 14.4 120.3 0.65 0.32 Ex. (334)P3-16 5.6 17.5 2500.0 14.3 124.3 0.65 0.31 Ex. (335) P3-17 5.6 17.22500.0 14.6 121.3 0.65 0.34 Ex. (336) P3-18 5.6 17.6 2500.0 14.2 124.60.66 0.31 Ex. (337) P3-19 5.6 17.1 2500.0 14.6 129.0 0.64 0.30 Ex. (338)P3-20 5.6 17.1 2500.0 14.6 125.9 0.65 0.33 Ex. (339) P3-21 5.5 17.52500.0 14.3 123.6 0.65 0.34 Ex. (340) P3-22 5.6 17.0 2500.0 14.7 122.60.65 0.31 Ex. (341) P3-23 5.5 17.3 2500.0 14.5 124.0 0.65 0.32 Ex. (342)P3-24 5.5 16.7 2500.0 14.9 127.4 0.65 0.32 Ex. (343) P3-25 5.5 17.62500.0 14.2 121.1 0.65 0.31 Ex. (344) P3-26 5.5 17.7 2500.0 14.1 127.20.66 0.34 Ex. (345) P3-27 5.6 17.7 2500.0 14.1 124.5 0.66 0.32 Ex. (346)P3-28 5.6 17.0 2500.0 14.7 121.5 0.65 0.31 Ex. (347) P3-29 5.5 17.12500.0 14.6 126.6 0.65 0.32 Ex. (348) P3-30 5.6 16.7 2500.0 14.9 128.70.65 0.32 Ex. (349) P3-31 5.6 17.3 2500.0 14.4 129.9 0.65 0.34 Ex. (350)P3-32 5.6 17.3 2500.0 14.5 124.3 0.64 0.32 Ex. (351) P3-33 5.6 16.82500.0 14.9 127.0 0.65 0.30 Ex. (352) P3-34 5.5 17.2 2500.0 14.6 125.50.66 0.32 Ex. (353) P3-35 5.6 16.9 2500.0 14.7 123.8 0.64 0.33 Ex. (354)P3-36 5.5 16.9 2500.0 14.8 127.7 0.66 0.31 Ex. (355) P3-37 5.5 16.72500.0 15.0 126.7 0.66 0.30 Ex. (356) P3-38 5.6 16.7 2500.0 15.0 125.30.65 0.31 Ex. (357) P4-2 5.0 12.8 2500.0 19.5 138.7 0.65 0.31 Ex. (358)P4-5 5.0 12.9 2500.0 19.4 132.7 0.65 0.32 Ex. (359) P4-8 5.1 13.2 2500.018.9 131.6 0.65 0.32 Ex. (360) P4-9 5.0 13.4 2500.0 18.6 132.7 0.65 0.31Ex. (361) P4-10 5.0 13.8 2500.0 18.2 139.3 0.66 0.34 Ex. (362) P4-17 5.214.9 2500.0 16.8 132.5 0.66 0.32 Ex. (363) P4-20 5.2 14.2 2500.0 17.6131.0 0.65 0.31 Ex. (364) P4-22 5.3 14.6 2500.0 17.1 130.8 0.65 0.32 Ex.(365) P4-24 5.2 14.0 2500.0 17.8 136.4 0.65 0.32

Example 366 An Emission-Auxiliary Layer (Green)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a compound of the present invention as anemission-auxiliary layer material

First, an ITO layer (anode) was formed on a glass substrate, and a filmof 2-TNATA was vacuum-deposited on the ITO layer to form a holeinjection layer with a thickness of 60 nm. Subsequently, NPD wasvacuum-deposited with a thickness of 60 nm on the hole injection layerto form a hole transport layer.

Subsequently, a film of the compound P1-21 of the present invention wasvacuum-deposited on the hole transport layer to form aemission-auxiliary layer with a thickness of 20 nm. A light emittinglayer with a thickness of 30 nm was deposited on the emission-auxiliarylayer by using the CBP as a host material and Ir(ppy)₃ as a dopantmaterial in a weight ratio of 95:5.

Next, a film of BAlq was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, and a film ofAlq₃ was formed with a thickness of 40 nm to form an electron transportlayer.

Next, LiF as halogenated alkali metal was deposited with a thickness of0.2 nm on the electron transport layer to form an electron injectionlayer, and then Al was deposited with a thickness of 150 nm on theelectron injection layer to form a cathode. In this way, the OLED wascompleted.

Example 367 to Example 485 An Emission-Auxiliary Layer (Green)

The OLED was manufactured in the same manner as described in TestExample 366, except that any one of the compounds P1-22 to P1-44, P1-77to P1-112, P2-21 to P2-44, and P2-77 to P2-112 of the present inventionin the Table 6 below was used as the emission-auxiliary layer material,instead of the inventive compound P1-21.

Comparative Example 9

An OLED was manufactured in the same manner as described in Test Example366, except that Comparative Compound 2 above was used as theemission-auxiliary layer material, instead of the inventive compoundP1-21.

Comparative Example 10

An OLED was manufactured in the same manner as described in Test Example366, except that Comparative Compound 3 above was used as theemission-auxiliary layer material, instead of the inventive compoundP1-21.

Comparative Example 11

An OLED was manufactured in the same manner as described in Test Example366, except that Comparative Compound 4 above was used as theemission-auxiliary layer material, instead of the inventive compoundP1-21.

Comparative Example 12

An OLED was manufactured in the same manner as described in Test Example366, except not to form the emission-auxiliary layer.

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough Test Examples 366 to 485 and Comparative Example 9 to 12, andelectro-luminescence (EL) characteristics of the OLED were measured byPR-650 (Photoresearch). Also, T95 life span was measured by life spanmeasuring equipment (Mcscience) at a reference brightness of 5000 cd/m².Table 6 below shows evaluation results of OLEDs manufactured TestExamples and Comparative Examples.

TABLE 6 Current Voltage Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) x y Com. Ex (9) Com. Com (2)5.6 13.6 5000.0 36.8 116.9 0.33 0.61 Com. Ex (10) Com. Com (3) 5.9 12.15000.0 41.2 116.5 0.33 0.61 Com. Ex (11) Com. Com (4) 6.2 11.4 5000.044.0 110.1 0.33 0.61 Com. Ex (12) — 5.6 21.7 5000.0 23.0 65.7 0.33 0.61Ex. (366) P1-21 6.1 10.4 5000.0 48.2 147.9 0.33 0.62 Ex. (367) P1-22 5.810.2 5000.0 49.0 114.2 0.33 0.62 Ex. (368) P1-23 5.8 10.1 5000.0 49.3104.8 0.33 0.61 Ex. (369) P1-24 5.8 10.1 5000.0 49.4 143.6 0.33 0.61 Ex.(370) P1-25 6.0 10.0 5000.0 49.8 126.5 0.33 0.62 Ex. (371) P1-26 5.910.1 5000.0 49.5 118.2 0.33 0.61 Ex. (372) P1-27 5.9 10.3 5000.0 48.4109.7 0.33 0.62 Ex. (373) P1-28 6.0 10.4 5000.0 48.3 131.0 0.33 0.62 Ex.(374) P1-29 5.8 10.4 5000.0 48.3 103.4 0.33 0.62 Ex. (375) P1-30 6.010.3 5000.0 48.8 116.9 0.33 0.61 Ex. (376) P1-31 6.1 10.4 5000.0 47.9112.7 0.33 0.62 Ex. (377) P1-32 6.1 10.1 5000.0 49.5 106.9 0.33 0.61 Ex.(378) P1-33 5.9 10.3 5000.0 48.6 104.9 0.33 0.62 Ex. (379) P1-34 5.710.5 5000.0 47.6 127.4 0.33 0.61 Ex. (380) P1-35 6.0 10.5 5000.0 47.4126.6 0.33 0.61 Ex. (381) P1-36 5.8 10.1 5000.0 49.7 140.1 0.33 0.62 Ex.(382) P1-37 5.7 10.3 5000.0 48.6 134.4 0.33 0.61 Ex. (383) P1-38 5.910.3 5000.0 48.4 142.4 0.33 0.61 Ex. (384) P1-39 6.1 10.2 5000.0 49.2129.9 0.33 0.62 Ex. (385) P1-40 6.0 10.5 5000.0 47.6 140.4 0.33 0.61 Ex.(386) P1-41 6.0 10.4 5000.0 48.1 145.4 0.33 0.61 Ex. (387) P1-42 5.910.3 5000.0 48.5 129.9 0.33 0.62 Ex. (388) P1-43 6.0 10.6 5000.0 47.1118.9 0.33 0.61 Ex. (389) P1-44 6.1 10.6 5000.0 47.2 114.1 0.33 0.62 Ex.(390) P1-77 5.9 10.4 5000.0 48.1 126.6 0.33 0.62 Ex. (391) P1-78 6.010.2 5000.0 48.8 140.4 0.33 0.61 Ex. (392) P1-79 6.2 10.2 5000.0 49.1131.8 0.33 0.61 Ex. (393) P1-80 5.8 10.3 5000.0 48.4 130.1 0.33 0.61 Ex.(394) P1-81 6.2 10.4 5000.0 48.1 115.5 0.33 0.62 Ex. (395) P1-82 6.110.2 5000.0 48.9 143.7 0.33 0.62 Ex. (396) P1-83 6.2 10.5 5000.0 47.5119.2 0.33 0.61 Ex. (397) P1-84 5.9 10.0 5000.0 50.0 128.0 0.33 0.62 Ex.(398) P1-85 5.9 10.6 5000.0 47.1 132.9 0.33 0.61 Ex. (399) P1-86 5.810.1 5000.0 49.6 115.8 0.33 0.61 Ex. (400) P1-87 5.8 10.1 5000.0 49.6137.4 0.33 0.61 Ex. (401) P1-88 5.8 10.4 5000.0 48.2 105.4 0.33 0.62 Ex.(402) P1-89 5.8 10.5 5000.0 47.5 109.9 0.33 0.62 Ex. (403) P1-90 5.810.2 5000.0 49.0 104.9 0.33 0.61 Ex. (404) P1-91 6.1 10.1 5000.0 49.3125.1 0.33 0.61 Ex. (405) P1-92 6.2 10.0 5000.0 49.8 109.0 0.33 0.61 Ex.(406) P1-93 6.0 10.6 5000.0 47.3 139.3 0.33 0.62 Ex. (407) P1-94 6.110.1 5000.0 49.3 143.5 0.33 0.62 Ex. (408) P1-95 5.8 10.3 5000.0 48.3148.4 0.33 0.62 Ex. (409) P1-96 6.2 10.2 5000.0 49.0 129.1 0.33 0.62 Ex.(410) P1-97 6.0 10.3 5000.0 48.5 120.9 0.33 0.62 Ex. (411) P1-98 5.810.6 5000.0 47.3 118.2 0.33 0.62 Ex. (412) P1-99 6.0 10.4 5000.0 48.2100.5 0.33 0.62 Ex. (413) P1-100 6.1 10.2 5000.0 49.0 110.1 0.33 0.61Ex. (414) P1-101 5.8 10.6 5000.0 47.3 103.9 0.33 0.62 Ex. (415) P1-1025.9 10.6 5000.0 47.4 118.9 0.33 0.62 Ex. (416) P1-103 5.9 10.3 5000.048.7 107.0 0.33 0.61 Ex. (417) P1-104 6.2 10.6 5000.0 47.2 112.5 0.330.62 Ex. (418) P1-105 6.2 10.0 5000.0 49.9 110.3 0.33 0.62 Ex. (419)P1-106 5.9 10.2 5000.0 49.0 141.6 0.33 0.61 Ex. (420) P1-107 6.0 10.45000.0 47.9 108.6 0.33 0.62 Ex. (421) P1-108 5.8 10.2 5000.0 48.9 130.00.33 0.62 Ex. (422) P1-109 5.9 10.6 5000.0 47.4 132.4 0.33 0.62 Ex.(423) P1-110 5.7 10.4 5000.0 48.3 132.7 0.33 0.61 Ex. (424) P1-111 5.910.0 5000.0 49.8 140.1 0.33 0.61 Ex. (425) P1-112 6.2 10.1 5000.0 49.7124.7 0.33 0.62 Ex. (426) P2-21 5.7 9.5 5000.0 52.4 149.6 0.33 0.61 Ex.(427) P2-22 6.0 9.1 5000.0 54.7 101.9 0.33 0.61 Ex. (428) P2-23 6.0 9.15000.0 54.8 103.2 0.33 0.61 Ex. (429) P2-24 6.1 9.4 5000.0 53.4 125.40.33 0.61 Ex. (430) P2-25 6.0 9.2 5000.0 54.2 141.2 0.33 0.62 Ex. (431)P2-26 6.0 9.3 5000.0 54.0 116.4 0.33 0.61 Ex. (432) P2-27 6.1 9.5 5000.052.6 138.5 0.33 0.61 Ex. (433) P2-28 6.0 9.4 5000.0 53.1 132.0 0.33 0.61Ex. (434) P2-29 6.0 9.9 5000.0 50.4 133.6 0.33 0.61 Ex. (435) P2-30 6.09.6 5000.0 52.2 117.4 0.33 0.61 Ex. (436) P2-31 6.0 9.2 5000.0 54.2149.9 0.33 0.61 Ex. (437) P2-32 6.0 9.7 5000.0 51.4 105.8 0.33 0.62 Ex.(438) P2-33 5.7 9.7 5000.0 51.8 135.1 0.33 0.62 Ex. (439) P2-34 6.1 9.55000.0 52.7 127.6 0.33 0.62 Ex. (440) P2-35 5.9 9.3 5000.0 54.0 137.80.33 0.62 Ex. (441) P2-36 5.8 9.7 5000.0 51.7 115.8 0.33 0.61 Ex. (442)P2-37 6.0 9.4 5000.0 53.4 142.9 0.33 0.61 Ex. (443) P2-38 6.0 9.6 5000.052.1 144.4 0.33 0.61 Ex. (444) P2-39 6.0 9.5 5000.0 52.4 126.3 0.33 0.62Ex. (445) P2-40 5.8 9.5 5000.0 52.6 128.5 0.33 0.61 Ex. (446) P2-41 5.89.6 5000.0 52.3 109.2 0.33 0.61 Ex. (447) P2-42 5.7 9.9 5000.0 50.7129.7 0.33 0.62 Ex. (448) P2-43 6.0 9.5 5000.0 52.7 110.0 0.33 0.61 Ex.(449) P2-44 6.0 9.9 5000.0 50.5 141.9 0.33 0.62 Ex. (450) P2-77 6.0 9.15000.0 54.7 128.6 0.33 0.62 Ex. (451) P2-78 5.7 9.9 5000.0 50.5 109.10.33 0.61 Ex. (452) P2-79 6.1 9.1 5000.0 54.9 100.5 0.33 0.62 Ex. (453)P2-80 6.0 9.9 5000.0 50.6 132.8 0.33 0.62 Ex. (454) P2-81 5.8 9.7 5000.051.3 141.8 0.33 0.61 Ex. (455) P2-82 5.9 9.7 5000.0 51.3 148.1 0.33 0.61Ex. (456) P2-83 5.9 9.2 5000.0 54.1 141.2 0.33 0.61 Ex. (457) P2-84 5.89.3 5000.0 53.6 142.6 0.33 0.61 Ex. (458) P2-85 5.8 9.6 5000.0 52.3129.5 0.33 0.61 Ex. (459) P2-86 6.0 9.2 5000.0 54.5 127.9 0.33 0.62 Ex.(460) P2-87 6.1 9.6 5000.0 52.3 112.8 0.33 0.61 Ex. (461) P2-88 5.8 9.45000.0 53.4 119.6 0.33 0.62 Ex. (462) P2-89 6.0 9.4 5000.0 53.2 101.30.33 0.62 Ex. (463) P2-90 5.9 9.6 5000.0 52.3 148.0 0.33 0.62 Ex. (464)P2-91 5.7 9.8 5000.0 50.9 136.2 0.33 0.62 Ex. (465) P2-92 5.8 9.2 5000.054.2 103.4 0.33 0.61 Ex. (466) P2-93 6.0 9.1 5000.0 54.8 137.7 0.33 0.62Ex. (467) P2-94 5.8 9.8 5000.0 51.1 131.6 0.33 0.62 Ex. (468) P2-95 6.09.7 5000.0 51.7 144.1 0.33 0.62 Ex. (469) P2-96 5.7 9.3 5000.0 53.6109.9 0.33 0.62 Ex. (470) P2-97 6.0 9.8 5000.0 50.9 120.6 0.33 0.62 Ex.(471) P2-98 6.0 9.1 5000.0 54.8 139.7 0.33 0.62 Ex. (472) P2-99 5.9 9.35000.0 53.9 125.5 0.33 0.62 Ex. (473) P2-100 6.0 9.3 5000.0 53.7 127.20.33 0.61 Ex. (474) P2-101 6.1 9.4 5000.0 53.3 137.4 0.33 0.62 Ex. (475)P2-102 6.2 9.9 5000.0 50.7 136.5 0.33 0.61 Ex. (476) P2-103 6.2 9.35000.0 53.5 115.7 0.33 0.62 Ex. (477) P2-104 6.1 9.8 5000.0 51.2 119.40.33 0.61 Ex. (478) P2-105 5.7 10.0 5000.0 50.0 125.9 0.33 0.61 Ex.(479) P2-106 6.1 9.2 5000.0 54.3 143.8 0.33 0.62 Ex. (480) P2-107 5.89.9 5000.0 50.4 105.0 0.33 0.62 Ex. (481) P2-108 5.8 9.7 5000.0 51.5107.6 0.33 0.61 Ex. (482) P2-109 5.8 9.2 5000.0 54.3 136.8 0.33 0.62 Ex.(483) P2-110 5.9 9.4 5000.0 53.3 121.4 0.33 0.62 Ex. (484) P2-111 5.79.6 5000.0 52.0 134.9 0.33 0.62 Ex. (485) P2-112 5.9 9.7 5000.0 51.6136.1 0.33 0.62

It can be seen from the results in Tables 5 and 6 above, that the OLEDsusing the inventive compounds as the auxiliary emission layer materialshowed predominantly improved efficiency and lifespan, compared to theOLEDs using comparative compounds 2 to 4 as the auxiliary emission layermaterial and the OLEDs not having the auxiliary emission layer.

That is, the OLEDs using the present invention compounds showedpredominantly improved efficiency and long life span, compared to theOLEDs not forming the auxiliary emission layer, and the OLEDs usingcomparative compounds 2 to 4 as the auxiliary emission layer material.

Especially, comparing the case that OLEDs employ comparative compounds 3and 4 and the case that OLEDs employ the inventive compounds, it can beseen that significant difference in efficiency and life span was shownbetween the compounds having a linker equally linked to the same2-position of the carbazole cores yet the substituent amine group islinked on a different position of the linker. This is believed becausedifferent bonding angle occurs depending on to which position of thelinker the amine group is linked, so does the different T1 values, whichcauses different electron blocking abilities.

In addition, referring to Table 5 showing the result in OLEDs comprisingred auxiliary emission layer, it can be seen that although efficiencyand driving voltage are similar or slightly increased, life span isimproved where compounds(P3-1 to P3-38) of the present invention havingR³ being a substituent other than hydrogen are used as a red auxiliaryemission layer, compared to the compounds having R³ being hydrogen. Itis inferred that this result is caused because when the layer of OLED isformed, packing density, Hole injection and mobility are dependent onthe kinds of substituent R³.

Further, the case that the inventive compounds(P4-2˜24) of which Ar² iscarabzole derivatives among the inventive compounds are employed as redauxiliary emission layer materials showed the best results, especially,showed predominantly improved efficiency and driving voltage. Theseresults are believed to come from that heat-degradation in theinterfacial between ITO and a hole transport layer is decreased and heatthe life span of the organic elements is improved because the abilitiesof a hole injection and a hole mobility are improved by comprisinganother carabzole derivatives in the inventive compound, and the drivingvoltage, efficiency and life span are optimized because charge balancebetween a hole and an electron in a light emitting layer is increasedand the light emitting is well made in the light emitting layer not theinterfacial of the hole transport layer by transferring more holes tothe light emitting layer.

Furthermore, in compounds(P4-2˜10) where Ar² is a carbazole derivativesand Ar² is linked to L(linker) on ortho position, the driving voltage ofthe organic element gets lower than in compounds(P4-17˜24) where Ar² isa carbazole derivatives and Ar² is linked to L (linker) on metaposition, because packing density of the compound where Ar² is linked toL (linker) on ortho position gets well during deposition.

As described above, it was shown that the linking position of betweenthe carbazole core and the linker substituted with a amine group,between the linker and the amine group, and the kind of the linker isimportant factor because the performance ability of the organic elementsin an auxiliary emission layer as well as a hole transport layer changesdepending on the linking position and the kind of the linker.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

1. A compound of Formula 1:

wherein, Ar¹ to Ar³ are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P; a fused ring formed by a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; anda C₆-C₃₀ aryloxy group, L is

m and o are each an integer of 0 to 4, n is an integer of 0 to 3, R¹, R²and R³ are each independently selected from the group consisting of i)deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P; a fused ring formed by a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; aC₆-C₃₀ aryloxy group; -L′-N(R^(a)) (R^(b)); and combinations thereof, orii) any two adjacent groups of R¹, R² and R³ may be optionally linkedtogether to form at least one ring, and the group(s) not forming a ringmay be the same as defined in the above i), L′ is selected from thegroup consisting of single bond; a C₆-C₆₀ arylene group; a fluorenylenegroup; a fused ring formed by a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring; and a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P,R^(a) and R^(b) are each independently selected from the groupconsisting of C₆-C₆₀ aryl group; a fluorenyl group; a fused ring formedby a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P, each of the above aryl group,fluorenyl group, heterocyclic group, fused ring group, alkyl group,alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene groupand fluorenylene group may be substituted with one or more substituentsselected from the group consisting of deuterium; halogen; a silanegroup; a siloxane group; a boron group; a germanium group; a cyanogroup; a nitro group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxy group; aC₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted with deuterium; afluorenyl group; a C₂-C₂₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P; aC₃-C₂₀ cycloalkyl group; a C₇-C₂₀ arylalkyl group; and a C₈-C₂₀arylalkenyl group.
 2. The compound of claim 1 represented by one ofFormulas below:

wherein, R′ and R″ are each independently selected from the groupconsisting of hydrogen; deuterium; tritium; a C₆-C₂₀ aryl group; aC₁-C₂₀ alkyl group; and a C₂-C₂₀ alkenyl group, and R′ and R″ may belinked together to form a spiro compound with the carbon to which theyare attached, p is an integer of 0 to 4, q is an integer of 0 to 3, R⁴and R⁵ are each independently selected from the group consisting of i)deuterium; tritium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; aC₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P; a fused ring formed bya C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkylgroup; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxylgroup; and a C₆-C₃₀ aryloxy group, and ii) any two adjacent groups of R⁴and R⁵ may be optionally linked together to form at least one ring, andthe groups of R⁴s and R⁵s not forming a ring may be the same as definedin the above.
 3. The compound of claim 1, wherein Ar² to Ar³ are eachindependently selected from the following structures:

wherein, Ar⁴ is selected from the group consisting of a C₆-C₆₀ arylgroup; a fluorenyl group; and a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, R⁶ and R⁷ are each independently selected from the groupconsisting of i) deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenylgroup; a C₂-C₆₀ heterocyclic group containing at least one heteroatomselected from the group consisting of O, N, S, Si, and P; a fused ringformed by a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀alkoxy group; a C₆-C₃₀ aryloxy group; and -L′-N(R^(a)) (R^(b)), wherein,L′ is selected from the group consisting of single bond; a C₆-C₆₀arylene group; a fluorenylene group; a fused ring formed by a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si, and P, and R^(a) and R^(b) are eachindependently selected from the group consisting of C₆-C₆₀ aryl group; afluorenyl group; a fused ring formed by a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, or ii) any two adjacent groups of R⁶ and R⁷ may be independentlylinked together to form at least one ring, and the groups of R⁶s and R⁷snot forming a ring may be the same as defined in the above i), a is aninteger of 0 to 4, wherein plural R⁶s may be same or different eachother when a is each 2 or more, b is an integer of 0 to 3, whereinplural R⁷s may be same or different each other when b is each 2 or more.4. The compound of claim 1, wherein o is 0 (zero), or R³ is selectedfrom the following structures:


5. The compound of claim 1, wherein at least one adjacent groups of R¹or R² is linked to form a ring.
 6. The compound of claim 5 representedby one of Formulas below:

wherein Ar¹ to Ar³, L, R¹, m and n are the same as defined in claim 1.7. The compound of claim 1 represented by one of Formulas below:

wherein Ar², Ar³, L, R¹, R², m and n are the same as defined in claim 1,X is O, S or C(R′) (R″), R′ and R″ are each independently selected fromthe group consisting of hydrogen; deuterium; tritium; a C₆-C₂₀ arylgroup; a C₁-C₂₀ alkyl group; and a C₂-C₂₀ alkenyl group, and R′ and R″may be linked together to form a spiro compound with the carbon to whichthey are attached, p is an integer of 0 to 4, q is an integer of 0 to 3,R⁴ and R⁵ are each independently selected from the group consisting ofi) deuterium; tritium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group;a C₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P; a fused ring formed bya C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkylgroup; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxylgroup; and a C₆-C₃₀ aryloxy group, and ii) any two adjacent groups of R⁴and R⁵ may be optionally linked together to form at least one ring, andthe groups of R⁴s and R⁵s not forming a ring may be the same as definedin the above.
 8. The compound of claim 1 represented by the followingFormula:

wherein R¹, R², m, n, Ar¹, Ar³ and L are the same as defined in Formula1, Ar⁴ is selected from the group consisting of a C₆-C₆₀ aryl group; afluorenyl group; and a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, R⁶and R⁷ are each independently selected from the group consisting of i)deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P; a fused ring formed by a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; aC₆-C₃₀ aryloxy group; and -L′-N(R^(a)) (R^(b)), wherein, L′ is selectedfrom the group consisting of single bond; a C₆-C₆₀ arylene group; afluorenylene group; a fused ring formed by a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, and R^(a) and R^(b) are each independently selected from thegroup consisting of C₆-C₆₀ aryl group; a fluorenyl group; a fused ringformed by a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and aC₂-C₆₀ heterocyclic group containing at least one heteroatom selectedfrom the group consisting of O, N, S, Si, and P, or ii) any two adjacentgroups may be independently linked together to form at least one ring,and the groups of R⁶s and R⁷s not forming a ring may be the same asdefined in the above i), a is an integer of 0 to 4, wherein plural R⁶smay be same or different each other when a is each 2 or more, b is aninteger of 0 to 3, wherein plural R⁷s may be same or different eachother when b is each 2 or more.
 9. The compound of claim 8 representedby the following Formulas:

wherein, R¹, R², R⁶, R⁷, a, b, m, n, Ar¹, Ar³, Ar⁴ and L are the same asdefined in claim
 8. 10. The compound of claim 1, wherein Formula 1 isany one of the compounds below:


11. An organic electric element comprising a first electrode, a secondelectrode, and an organic material layer disposed between the firstelectrode and the second electrode, wherein the organic material layercomprises the compound of claim
 1. 12. The organic electric element ofclaim 11, wherein the organic material layer comprises at least one of ahole injection layer, a hole transport layer, an emission-auxiliarylayer and an emitting layer, and at least one of the layers comprisesthe compound in the same kind or two or more different kinds.
 13. Theorganic electric element of claim 11, wherein the organic electricelement further comprises at least one layer to improve luminescenceefficiency, formed on at least one of the sides of the first and secondelectrodes opposite to the organic material layer.
 14. The organicelectric element of claim 11, wherein the organic material layer isformed by any one of the processes of spin coating, nozzle printing,inkjet printing, slot coating, dip coating and roll-to-roll.
 15. Anelectronic device comprising a display device, which comprises theorganic electric element of claim 11, and a control unit for driving thedisplay device.
 16. The electronic device of claim 15, wherein theorganic electric element comprises at least one of an organic lightemitting diode, an organic solar cell, an organic photo conductor, anorganic transistor, and an element for monochromatic or whiteillumination.